[ CAS No. 1670-83-3 ] {[proInfo.proName]}

Name: 1670-83-3|Indole-7-carboxylic acid|98%
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Quality Control of [ 1670-83-3 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 1670-83-3 ]

CAS No. :	1670-83-3	MDL No. :	MFCD00210442
Formula :	C₉H₇NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IPDOBVFESNNYEE-UHFFFAOYSA-N
M.W :	161.16	Pubchem ID :	74281
Synonyms :

Calculated chemistry of [ 1670-83-3 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	45.26
TPSA :	53.09 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.17 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.28
Log Po/w (XLOGP3) :	1.57
Log Po/w (WLOGP) :	1.87
Log Po/w (MLOGP) :	1.08
Log Po/w (SILICOS-IT) :	1.89
Consensus Log Po/w :	1.54

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.32
Solubility :	0.776 mg/ml ; 0.00482 mol/l
Class :	Soluble
Log S (Ali) :	-2.3
Solubility :	0.817 mg/ml ; 0.00507 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.65
Solubility :	0.364 mg/ml ; 0.00226 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.01

Safety of [ 1670-83-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1670-83-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 1670-83-3 ]
Downstream synthetic route of [ 1670-83-3 ]

[ 1670-83-3 ] Synthesis Path-Upstream 1~13

1
[ 51417-51-7 ]
[ 201230-82-2 ]
[ 1670-83-3 ]

Reference： [1] Organic Letters, 2004, vol. 6, # 1, p. 7 - 10

2
[ 68109-89-7 ]
[ 1670-83-3 ]

Reference： [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1986, vol. 22, # 1, p. 36 - 37[2] Khimiya Geterotsiklicheskikh Soedinenii, 1986, vol. 22, # 1, p. 44 - 45

3
[ 15861-40-2 ]
[ 1670-83-3 ]

Reference： [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 24, p. 4692 - 4703

4
[ 496-15-1 ]
[ 1670-83-3 ]

Reference： [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 24, p. 4692 - 4703

5
[ 34851-15-5 ]
[ 1670-83-3 ]

Reference： [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 24, p. 4692 - 4703

6
[ 34851-16-6 ]
[ 1670-83-3 ]

Reference： [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 24, p. 4692 - 4703

7
[ 96631-87-7 ]
[ 1670-83-3 ]

Reference： [1] Journal of the American Chemical Society, 1955, vol. 77, p. 5700

8
[ 28899-75-4 ]
[ 1670-83-3 ]

Reference： [1] Journal of the American Chemical Society, 1955, vol. 77, p. 5700

9
[ 77158-85-1 ]
[ 1670-83-3 ]

Reference： [1] Journal of the American Chemical Society, 1955, vol. 77, p. 5700

10
[ 5437-38-7 ]
[ 1670-83-3 ]

Reference： [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1986, vol. 22, # 1, p. 36 - 37[2] Khimiya Geterotsiklicheskikh Soedinenii, 1986, vol. 22, # 1, p. 44 - 45

11
[ 1670-83-3 ]
[ 1074-88-0 ]

Reference： [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 9, p. 3725 - 3732

12
[ 67-56-1 ]
[ 1670-83-3 ]
[ 93247-78-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: for 20 h; Reflux Stage #2: With sodium hydrogencarbonate In ethyl acetate	To a solution of 1 H-indole-7-carboxylic acid (20 g, 124 mmol, 1 .0 eq) in MeOH (700 ml) was added H2S04 (1.2 g, 12 mmol, 0.1 eq) and the mixture was stirred at reflux for 20 hrs. Then, MeOH was evaporated by rotavapor and the residue was dissolved in ethyl acetate. The organic phase was washed with saturated Na2C03, brine, dried over Na2S04 and filtered. The solvent was removed under reduced pressure to give intermediate 1 (16.3 g, 75percent yield) as a yellow solid.

Reference： [1] Patent: WO2013/4709, 2013, A1, . Location in patent: Page/Page column 51

13
[ 1670-83-3 ]
[ 18107-18-1 ]
[ 93247-78-0 ]

Yield	Reaction Conditions	Operation in experiment
13.7%	at 20℃; for 0.5 h;	1 g of indole-7-carboxylic acid was dissolved in 10 ml of methanol. 5 ml of trimethylsilyl diazomethane was added and the mixture was allowed to stand at room temperature for 30 minutes. 1 N acetic acid was added until the reaction solution became colorless, and the solvent was distilled off. The obtained substance was dissolved in distillation and adjusted to pH 8 and extracted with ethyl acetate. The ethyl acetate phase obtained was dried with anhydrous magnesium sulfate. This was dissolved in acetone and recrystallized, and the solvent was distilled off. As a result, 148.7 mg (yield: 13.7percent) of a compound was obtained. NMR, mass spectrum and melting point of this compound were measured, and the compound 4 having the structure of the general formula 5 was confirmed.

Reference： [1] Patent: JP2018/52865, 2018, A, . Location in patent: Paragraph 0040

[ 1670-83-3 ] Synthesis Path-Downstream 1~88

1
[ 85-44-9 ]
[ 1670-83-3 ]
[ 93217-27-7 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1989,vol. 25,p. 761 - 764
Khimiya Geterotsiklicheskikh Soedinenii,1989,p. 915 - 918

2
[ 1670-83-3 ]
[ 111669-24-0 ]
1-(indolyl-7-carbonyl)-4-<3-(ethylamino)-2-pyridyl>piperazine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 999 - 1014

3
[ 68109-89-7 ]
[ 1670-83-3 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1986,vol. 22,p. 36 - 37
Khimiya Geterotsiklicheskikh Soedinenii,1986,vol. 22,p. 44 - 45

4
[ 1670-83-3 ]
[ 593252-37-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1897 - 1901

5
[ 1670-83-3 ]
6-[(1H-indole-7-carbonyl)-amino]-hexanoyl chloride [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1897 - 1901

6
[ 1670-83-3 ]
7-[(1H-indole-7-carbonyl)-amino]-heptanoyl chloride [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1897 - 1901

7
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (5-hydroxycarbamoyl-pentyl)-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1897 - 1901
[2]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1897 - 1901

8
[ 1670-83-3 ]
[ 593252-43-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1897 - 1901

9
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (6-hydroxycarbamoyl-hexyl)-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1897 - 1901
[2]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1897 - 1901

10
[ 496-15-1 ]
[ 1670-83-3 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4692 - 4703

11
[ 34851-15-5 ]
[ 1670-83-3 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4692 - 4703

12
[ 34851-16-6 ]
[ 1670-83-3 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 4692 - 4703

13
[ 5437-38-7 ]
[ 1670-83-3 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1986,vol. 22,p. 36 - 37
Khimiya Geterotsiklicheskikh Soedinenii,1986,vol. 22,p. 44 - 45

14
[ 28899-75-4 ]
[ 1670-83-3 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 5700

15
[ 77158-85-1 ]
[ 1670-83-3 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 5700

16
[ 1670-83-3 ]
[ 109-89-7 ]
1H-indole-7-carboxylic acid diethylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 4h;	A solution of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> (0.48 g, 3 mmol), diethylamine (0.93 mL, 9 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.74 g, 9 mmol), 1-hydroxybenzotriazole (1.23 g, 9 mmol), triethylamine (1.26 mL, 12 mmol) in dimethylformamide (30 mL) is stirred at room temperature for 4 hours. The mixture is diluted with ethyl acetate, washed with 1N HCl, water, a saturated aqueous sodium hydrogen carbonate solution, water, and a saturated brine, dried over magnesium sulfate, and concentrated to give the desired 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> diethylamide (0.64 g, yield: 99 %). 1H-NMR (CDCl3) delta: 1.27 (6H, t, J=7.1Hz), 3.56 (4H, q, J=7.1Hz), 6.56 (1H, dd, J=2.2, 3.2Hz), 7.09 (1H, t, J=7.5Hz), 7.23 (1H, dd, J=0.7, 7.3Hz), 7.25-7.27 (1H, m), 7.70 (1H, d, J=7.9Hz), 9.06 (1H, brs).

Reference： [1]Patent: EP1514869,2005,A1 .Location in patent: Page/Page column 25

17
(4-tert-butyl-benzyl)-(3-methyl-butyl)-amine [ No CAS ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-(3-methyl-butyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 2.08h;	Example 1; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-(3-methyl-butyl)-amide 1 and Other Compounds of Formula I; To a solution of 48 mg of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> (0.3 mmol) and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 70 mg (0.3 mmol) of (4-tert-butyl-benzyl)-(3-methyl-butyl)-amine in 1 ml DMF were added. After stirring for 2 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The resulting orange oil was purified by column chromatography (8 g silica gel; heptane/EtOAc 4:1) to give 101 mg (86%) of a light yellow solid. MS (ISP) 377.5 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 55

18
(4-tert-butyl-benzyl)-pent-4-enyl-amine [ No CAS ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-pent-4-enyl-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 2.08h;	Example 2; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-pent-4-enyl-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 69 mg (0.3 mmol) of (4-tert-butyl-benzyl)-pent-4-enyl-amine in 1 ml DMF was added. After stirring for 2 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The resulting oil was purified by column chromatography (8 g silica gel; heptane/EtOAc 6:1) to give 62 mg (53%) of a light yellow viscous oil. MS (ISP) 375.5 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 60

19
(4-tert-butyl-benzyl)-(4,4,4-trifluoro-butyl)-amine [ No CAS ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-(4,4,4-trifluoro-butyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 19.08h;	Example 3; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-(4,4,4-trifluoro-butyl)-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 82 mg (0.3 mmol) of (4-tert-butyl-benzyl)-(4,4,4-trifluoro-butyl)-amine in 1 ml DMF were added. After stirring for 19 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo to give 130 mg (99%) of an orange solid. MS (ISP) 416.2 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 60

20
(4-tert-butyl-benzyl)-[2-(tetrahydro-thiopyran-4-yl)-ethyl]-amine [ No CAS ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(tetrahydro-thiopyran-4-yl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 24.08h;	Example 4; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(tetrahydro-thiopyran-4-yl)-ethyl]-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 78 mg (0.3 mmol) of (4-tert-butyl-benzyl)-[2-(tetrahydro-thiopyran-4-yl)-ethyl]-amine in 1 ml DMF were added. After stirring for 24 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo to give 134 mg (99%) of a yellow solid. MS (ISP) 435.5 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 60

21
[rac]-(4-tert-butyl-benzyl)-[3-(5-methyl-furan-2-yl)-butyl]-amine [ No CAS ]
[ 1670-83-3 ]
[rac]-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[3-(5-methyl-furan-2-yl)-butyl]amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 2.08h;	Example 5; Preparation of [rac]-<strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[3-(5-methyl-furan-2-yl)-butyl]-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 90 mg (0.3 mmol) of [rac]-(4-tert-butyl-benzyl)-[3-(5-methyl-furan-2-yl)-butyl]-amine in 1 ml DMF were added. After stirring for 2 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The orange residue was purified by column chromatography (8 g silica gel; heptane/EtOAc 6:1) to give 87 mg (63%) of a colorless viscous oil. MS (ISP) 443.5 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 60

22
[ 875305-06-9 ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(4-fluoro-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 4.08h;	Example 6; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(4-fluoro-phenyl)-ethyl]-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 86 mg (0.3 mmol) of (4-tert-butyl-benzyl)-[2-(4-fluoro-phenyl)-ethyl]-amine in 1 ml DMF were added. After stirring for 4 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The orange residue was purified by column chromatography (8 g silica gel; heptane/EtOAc 6:1) to give 107 mg (82%) of a white solid. MS (ISP) 429.6 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 60-61

23
(4-tert-butyl-benzyl)-[2-(4-methoxy-phenyl)-ethyl]-amine [ No CAS ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(4-methoxy-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 2.58h;	Example 7; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(4-methoxy-phenyl)-ethyl]-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 89 mg (0.3 mmol) (4-tert-butyl-benzyl)-[2-(4-methoxy-phenyl)-ethyl]-amine in 1 ml DMF was added. After 2.5 h stirring at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The yellow solid foam was purified by column chromatography (8 g silica gel; heptane/EtOAc 6:1) to give 107 mg (80%) of a white solid. MS (ISP) 441.4 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 61

24
[ 875305-08-1 ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-(2-p-tolyl-ethyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 3.08h;	Example 8; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-(2-p-tolyl-ethyl)-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 89 mg (0.3 mmol) (4-tert-butyl-benzyl)-(2-p-tolyl-ethyl)-amine in 1 ml DMF was added. After stirring for 3 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The yellow residue was purified by column chromatography (8 g silica gel; heptane/EtOAc 9:1) to give 111 mg (86%) of a white solid. MS (ISP) 425.3 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 61

25
(4-tert-butyl-benzyl)-[2-(3-fluoro-phenyl)-ethyl]-amine [ No CAS ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3-fluoro-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 3.08h;	Example 10; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(3-fluoro-phenyl)-ethyl]-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 86 mg (0.3 mmol) (4-tert-butyl-benzyl)-[2-(3-fluoro-phenyl)-ethyl]-amine in 1 ml DMF was added. After stirring for 3 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The orange residue was purified by column chromatography (8 g silica gel; heptane/EtOAc 9:1) to give 112 mg (86%) of a yellow solid. MS (EI) 428.2 (M)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 61

26
(4-tert-butyl-benzyl)-[2-(2-fluoro-phenyl)-ethyl]-amine [ No CAS ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(2-fluoro-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 3.08h;	Example 12; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(2-fluoro-phenyl)-ethyl]-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 86 mg (0.3 mmol) (4-tert-butyl-benzyl)-[2-(2-fluoro-phenyl)-ethyl]-amine in 1 ml DMF was added. After stirring for 3 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The yellow residue was purified by column chromatography (8 g silica gel; heptane/EtOAc 9:1) to give 111 mg (83%) of a white solid. MS (ISP) 429.6 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 62

27
[ 875305-13-8 ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 3.08h;	Example 13; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-ethyl]-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 91 mg (0.3 mmol) (4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-ethyl]-amine in 1 ml DMF was added. After stirring for 3 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The yellow solid foam was purified by column chromatography (8 g silica gel; heptane/EtOAc 9:1) to give 128 mg (86%) of a white solid. MS (ISP) 445.4 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 62

28
[ 875305-16-1 ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3-chloro-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 2.58h;	Example 15; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(3-chloro-phenyl)-ethyl]-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 91 mg (0.3 mmol) (4-tert-butyl-benzyl)-[2-(3-chloro-phenyl)-ethyl]-amine in 1 ml DMF was added. After 2.5 h stirring at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The yellow solid foam was purified by column chromatography (8 g silica gel; heptane/EtOAc 9:1) to give 122 mg (90%) of a white semisolid. MS (EI) 444.2 (M)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 62

29
[ 875305-17-2 ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 2.58h;	Example 16; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 101 mg (0.3 mmol) of (4-tert-butyl-benzyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine in 1 ml DMF were added. After 2.5 h stirring at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The yellow solid foam was purified by column chromatography (8 g silica gel; heptane/EtOAc 9:1) to give 124 mg (84%) of a colorless gum. MS (ISP) 479.5 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 62

30
(4-tert-butyl-benzyl)-[2-(2-chloro-phenyl)-ethyl]-amine [ No CAS ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(2-chloro-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 2.08h;	Example 17; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(2-chloro-phenyl)-ethyl]-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 95 mg (0.3 mmol) (4-tert-butyl-benzyl)-[2-(2-chloro-phenyl)-ethyl]-amine in 1 ml DMF was added. After stirring for 2 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The yellow solid foam was purified by column chromatography (8 g silica gel; heptane/EtOAc 9:1) to give 127 mg (90%) of a white solid. MS (ISP) 445.4 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 62

31
[ 875305-21-8 ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 1.58h;	Example 18; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 95 mg (0.3 mmol) (4-tert-butyl-benzyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amine in 1 ml DMF was added. After 1.5 h stirring at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The yellow solid foam was purified by column chromatography (8 g silica gel; heptane/EtOAc 9:1) to give 137 mg (94%) of a white solid. MS (ISP) 479.5 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 63

32
(4-tert-butyl-benzyl)-[2-(2,6-dichloro-phenyl)-ethyl]-amine [ No CAS ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(2,6-dichloro-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 2.08h;	Example 19; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(2,6-dichloro-phenyl)-ethyl]-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 106 mg (0.3 mmol) (4-tert-butyl-benzyl)-[2-(2,6-dichloro-phenyl)-ethyl]-amine in 1 ml DMF was added. After stirring for 2 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was crystallized from diethylether, leading to 123 mg white solid (85%). MS (ISP) 479.5 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 63

33
[ 875305-23-0 ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3,5-difluoro-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 4.08h;	Example 20; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(3,5-difluoro-phenyl)-ethyl]-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 91 mg (0.3 mmol) (4-tert-butyl-benzyl)-[2-(3,5-difluoro-phenyl)-ethyl]-amine in 1 ml DMF was added. After stirring for 4 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; EtOAc/heptane 1:6) to give 97 mg off-white solid (71%). MS (ISP) 447.3 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 63

34
(4-tert-butyl-benzyl)-[2-(4-trifluoromethyl-phenyl)-ethyl]-amine [ No CAS ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(4-trifluoromethyl-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 17.08h;	Example 21; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(4-trifluoromethyl-phenyl)-ethyl]-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 101 mg (0.3 mmol) (4-tert-butyl-benzyl)-[2-(4-trifluoromethyl-phenyl)-ethyl]-amine in 1 ml DMF was added. After stirring for 17 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; EtOAc/heptane 1:9) to give 110 mg colorless viscous oil (71%). MS (ISP) 479.5 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 63

35
[ 875305-25-2 ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3,4-difluoro-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 18.08h;	Example 22; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(3,4-difluoro-phenyl)-ethyl]-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 91 mg (0.3 mmol) (4-tert-butyl-benzyl)-[2-(3,4-difluoro-phenyl)-ethyl]-amine in 2 ml DMF was added. After stirring for 18 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; EtOAc/heptane 1:6) to give 95 mg light yellow viscous oil (66%). MS (ISP) 447.2 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 63

36
[ 289488-42-2 ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-phenethyl-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 5.08h;	Example 23; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-phenethyl-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 80 mg (0.3 mmol) of (4-tert-butyl-benzyl)-phenethyl-amine in 1 ml DMF were added. After stirring for 5 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; EtOAc/heptane 1:6) to give 100 mg white solid (80%). MS (ISP) 411.5 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 63

37
(4-tert-butyl-benzyl)-[2-(3-fluoro-4-trifluoromethyl-phenyl)-ethyl]-amine [ No CAS ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3-fluoro-4-trifluoromethyl-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 16.08h;	Example 24; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(3-fluoro-4-trifluoromethyl-phenyl)-ethyl]-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 3 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 106 mg (0.3 mmol) of (4-tert-butyl-benzyl)-[2-(3-fluoro-4-trifluoromethyl-phenyl)-ethyl]-amine in 2 ml DMF were added. After stirring for 16 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; EtOAc/heptane 1:6) to give 138 mg light yellow solid (91%). MS (ISP) 497.4 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 63

38
[ 875305-29-6 ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3-trifluoromethoxy-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 3.08h;	Example 25; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(3-trifluoromethoxy-phenyl)-ethyl]-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 3 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 105 mg (0.3 mmol) of (4-tert-butyl-benzyl)-[2-(3-trifluoromethoxy-phenyl)-ethyl]-amine in 2 ml DMF were added. After stirring for 3 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; EtOAc/heptane 1:6) to give 99 mg light yellow viscous oil (66%). MS (ISP) 495.5 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 64

39
[ 875305-31-0 ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(4-fluoro-3-trifluoromethyl-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 3.08h;	Example 26; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(4-fluoro-3-trifluoromethyl-phenyl)-ethyl]-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 3 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 106 mg (0.3 mmol) of (4-tert-butyl-benzyl)-[2-(4-fluoro-3-trifluoromethyl-phenyl)-ethyl]-amine in 2 ml DMF were added. After stirring for 3 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; EtOAc/heptane 1:9) to give 113 mg light yellow viscous oil (72%). MS (ISP) 497.4 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 64

40
(4-tert-butyl-benzyl)-[2-(2-fluoro-3-trifluoromethyl-phenyl)-ethyl]-amine [ No CAS ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(2-fluoro-3-trifluoromethyl-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 4.08h;	Example 27; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(2-fluoro-3-trifluoromethyl-phenyl)-ethyl]-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 3 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 106 mg (0.3 mmol) of (4-tert-butyl-benzyl)-[2-(2-fluoro-3-trifluoromethyl-phenyl)-ethyl]-amine in 2 ml DMF were added. After stirring for 4 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; EtOAc/heptane 1:6) to give 112 mg light yellow solid (73%). MS (ISP) 497.4 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 64

41
(4-tert-butyl-benzyl)-[2-(4-difluoromethoxy-phenyl)-ethyl]-amine [ No CAS ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(4-difluoromethoxy-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 2.58h;	Example 28; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(4-difluoromethoxy-phenyl)-ethyl]-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 3 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 105 mg (0.3 mmol) of (4-tert-butyl-benzyl)-[2-(4-difluoromethoxy-phenyl)-ethyl]-amine in 2 ml DMF were added. After 2.5 h stirring at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; EtOAc/heptane 1:6) to give 114 mg white solid (68%). MS (ISP) 477.4 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 64

42
[ 875305-37-6 ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[(R)-2-(4-chloro-phenyl)-2-hydroxy-ethyl]amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 24.08h;	Example 31; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[(R)-2-(4-chloro-phenyl)-2-hydroxy-ethyl]-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 3 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 95 mg (0.3 mmol) of (4-tert-butyl-benzyl)-[(R)-2-(4-chloro-phenyl)-2-hydroxy-ethyl]-amine were added. After stirring for 24 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; EtOAc/heptane 1:6) to give 72 mg light yellow solid (50%). MS (ISP) 461.4 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 64-65

43
(4-tert-butyl-benzyl)-(3-phenyl-propyl)-amine [ No CAS ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-(3-phenyl-propyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 4.08h;	Example 33; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-(3-phenyl-propyl)-amide; To a solution of 120 mg (0.74 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 240 mg of TBTU (0.74 mmol) in 8 ml DMF, were added 0.64 ml (3.72 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 280 mg (0.74 mmol) of (4-tert-butyl-benzyl)-(3-phenyl-propyl)-amine were added. After stirring for 4 h at rt, the reaction mixture was diluted with 80 ml water and extracted with EtOAc (2×). The combined organic phases were washed with brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (40 g silica gel; EtOAc/heptane 1:4) to give 205 mg white solid (63%). MS (ISP) 425.5 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 65

44
(4-tert-butyl-benzyl)-[2-(3-ethoxy-phenyl)-ethyl]-amine [ No CAS ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3-ethoxy-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 4.08h;	Example 34; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(3-ethoxy-phenyl)-ethyl]-amide; To a solution of 120 mg (0.74 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 240 mg of TBTU (0.74 mmol) in 8 ml DMF, were added 0.64 ml (3.72 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 309 mg (0.94 mmol) of (4-tert-butyl-benzyl)-[2-(3-ethoxy-phenyl)-ethyl]-amine were added. After stirring for 4 h at rt, the reaction mixture was diluted with 80 ml water and extracted with EtOAc (2×). The combined organic phases were washed with brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (40 g silica gel; EtOAc/heptane 1:4) to give 110 mg off-white foam (31%). MS (ISP) 455.7 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 65

45
[ 875305-43-4 ]
[ 1670-83-3 ]
[rac]-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3,4-dichloro-phenyl)-2-hydroxy-ethyl]amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 17.08h;	Example 40; Preparation of [rac]-<strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(3,4-dichloro-phenyl)-2-hydroxy-ethyl]-amide; To a solution of 36 mg (0.22 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 72 mg of TBTU (0.22 mmol) in 3 ml DMF, were added 0.19 ml (1.12 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 79 mg (0.22 mmol) of [rac]-(4-tert-butyl-benzyl)-[2-(3,4-dichloro-phenyl)-2-hydroxy-ethyl]-amine was added. After stirring for 17 h at rt, the reaction mixture was diluted with 30 ml water and extracted with EtOAc (2×). The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; heptane/EtOAc 2:1) to give 68 mg (59%) of an off-white solid. MS (ISP) 495.4 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 66

46
[ 875305-44-5 ]
[ 1670-83-3 ]
[rac]-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(4-fluoro-phenyl)-2-hydroxy-ethyl]amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 17.08h;	Example 42; Preparation of [rac]-<strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(4-fluoro-phenyl)-2-hydroxy-ethyl]-amide; To a solution of 80 mg (0.5 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 159 mg of TBTU (0.5 mmol) in 6 ml DMF, were added 0.43 ml (2.48 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 150 mg (0.5 mmol) of [rac]-(4-tert-butyl-benzyl)-[2-(4-fluoro-phenyl)-2-hydroxy-ethyl]-amine were added. After stirring for 17 h at rt, the reaction mixture was diluted with 60 ml water and extracted with EtOAc (2×). The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (40 g silica gel; heptane/EtOAc 2:1) to give 150 mg (66%) of an white solid. MS (ISP) 445.4 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 66

47
[ 875305-45-6 ]
[ 1670-83-3 ]
[rac]-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-2-hydroxy-ethyl]amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 17.08h;	Example 46; Preparation of [rac]-<strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-2-hydroxy-ethyl]-amide; To a solution of 50 mg (0.31 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 97 mg of TBTU (0.31 mmol) in 4 ml DMF, were added 0.27 ml (1.55 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 99 mg (0.31 mmol) of [rac]-(4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-2-hydroxy-ethyl]-amine were added. After stirring for 17 h at rt, the reaction mixture was diluted with 40 ml water and extracted with EtOAc (2×). The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; heptane/EtOAc 2:1) to give 89 mg (61%) of a white solid. MS (ISP) 461.4 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 67

48
[ 875305-52-5 ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3-chloro-4-fluoro-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 3.08h;	Example 55; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(3-chloro-4-fluoro-phenyl)-ethyl]-amide; To a solution of 48 mg (0.3 mmol) 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 3 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 96 mg (0.3 mmol) of (4-tert-butyl-benzyl)-[2-(3-chloro-4-fluoro-phenyl)-ethyl]-amine in 2 ml DMF were added. After stirring for 3 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo to give 141 mg white solid (99%). MS (ISP) 463.4 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 69

49
[ 875305-54-7 ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(2-fluoro-5-trifluoromethyl-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 3.83h;	Example 57; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(2-fluoro-5-trifluoromethyl-phenyl)-ethyl]-amide; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 3 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 118 mg (0.3 mmol) (4-tert-butyl-benzyl)-[2-(2-fluoro-5-trifluoromethyl-phenyl)-ethyl]-amine in 2 ml DMF was added. After 3¾ h stirring at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; EtOAc/heptane 1:9) to give 120 mg light yellow viscous oil (77%). MS (EI) 496.3 (M)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 69

50
[ 875305-68-3 ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3-difluoromethoxy-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 2.58h;	Example 64; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(3-difluoromethoxy-phenyl)-ethyl]-amide 68; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 3 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 100 mg (0.3 mmol) of (4-tert-butyl-benzyl)-[2-(3-difluoromethoxy-phenyl)-ethyl]-amine in 2 ml DMF was added. After 2.5 h stirring at rt, the reaction mixture was diluted with 50 ml water and extracted with EtOAc (2×). The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; EtOAc/heptane 1:6) to give 105 mg colorless viscous oil (73%). MS (EI) 477.4 (M)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 70

51
[ 875305-69-4 ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3-chloro-2-fluoro-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 4.08h;	Example 65; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(3-chloro-2-fluoro-phenyl)-ethyl]-amide 69; To a solution of 48 mg (0.3 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 96 mg of TBTU (0.3 mmol) in 3 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 96 mg (0.3 mmol) of (4-tert-butyl-benzyl)-[2-(3-chloro-2-fluoro-phenyl)-ethyl]-amine in 2 ml DMF were added. After stirring for 4 h at rt, the reaction mixture was diluted with 50 ml water and extracted with EtOAc (2×). The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; EtOAc/heptane 1:6) to give 103 mg white solid (73%). MS (EI) 464.1 (M)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 70-71

52
[rac]-(4-tert-butyl-benzyl)-(3,3,3-trifluoro-2-hydroxy-propyl)-amine [ No CAS ]
[ 1670-83-3 ]
[rac]-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-(3,3,3-trifluoro-2-hydroxy-propyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 4.08h;	Example 71; Preparation of [rac]-<strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-(3,3,3-trifluoro-2-hydroxy-propyl)-amide 75; To a solution of 30 mg (0.19 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 60 mg of TBTU (0.19 mmol) in 6 ml DMF, were added 0.16 ml (0.93 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 85 mg (0.19 mmol) of [rac]-(4-tert-butyl-benzyl)-(3,3,3-trifluoro-2-hydroxy-propyl)-amine were added. After stirring for 4 h at rt, the reaction mixture was diluted with 60 ml water and extracted with EtOAc (2×). The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (9 g silica gel; EtOAc/heptane 1:4) to give 17 mg white solid (17%). MS (EI) 418.2 (M)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 71

53
[ 875305-74-1 ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid butyl-(4-tert-butyl-benzyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 2.08h;	Example 73; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> butyl-(4-tert-butyl-benzyl)-amide 77; To a solution of 110 mg of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> (0.68 mmol) and 220 mg of TBTU (0.68 mmol) in 10 ml DMF, were added 0.59 ml (3.42 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 150 mg (0.68 mmol) of butyl-(4-tert-butyl-benzyl)-amine were added. After stirring for 2 h at rt, the reaction mixture was diluted with 100 ml water and extracted twice with EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; heptane/EtOAc 2:1) to give 209 mg (82%) of a light yellow viscous oil. MS (EI) 362.2 (M)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 72

54
(4-tert-butyl-benzyl)-[2-(3-methoxy-phenyl)-ethyl]-amine [ No CAS ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3-methoxy-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 3.08h;	Example 74; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(3-methoxy-phenyl)-ethyl]-amide 78; To a solution of 80 mg of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> (0.5 mmol) and 159 mg of TBTU (0.5 mmol) in 10 ml DMF, were added 0.425 ml (2.48 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 174 mg (0.68 mmol) of (4-tert-butyl-benzyl)-[2-(3-methoxy-phenyl)-ethyl]-amine were added. After stirring for 3 h at rt, the reaction mixture was diluted with 50 ml water and extracted twice with EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (40 g silica gel; heptane/EtOAc 2:1) to give 168 mg (75%) of a white solid. MS (ISP) 441.4 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 72

55
[rac]-(4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-propyl]-amine [ No CAS ]
[ 1670-83-3 ]
[rac]-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-propyl]amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 22.08h;	Example 75; Preparation of [rac]-<strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-propyl]-amide 79; To a solution of 81 mg of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> (0.5 mmol) and 161 mg of TBTU (0.5 mmol) in 2 ml DMF, were added 0.43 ml (2.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 158 mg (0.5 mmol) [rac]-(4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-propyl]-amine in 3.5 ml DMF was added. After stirring for 22 h at rt, the reaction mixture was diluted with 50 ml water and extracted twice with EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (40 g silica gel; heptane/EtOAc 2:1) to give 203 mg (86%) of a off-white solid. MS(ISP) 459.4 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 72

56
(4-tert-butyl-benzyl)-[2-(2,4-dichloro-phenyl)-ethyl]-amine [ No CAS ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(2,4-dichloro-phenyl)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 3.08h;	Example 76; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(2,4-dichloro-phenyl)-ethyl]-amide 80; To a solution of 81 mg of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> (0.5 mmol) and 161 mg of TBTU (0.5 mmol) in 10 ml DMF, were added 0.43 ml (2.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 168 mg (0.5 mmol) of (4-tert-butyl-benzyl)-[2-(2,4-dichloro-phenyl)-ethyl]-amine were added. After stirring for 3 h at rt, the reaction mixture was diluted with 50 ml water and extracted twice with EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (40 g silica gel; heptane/EtOAc 2:1) to give 213 mg (87%) of a light yellow oil. MS(ISP) 479.4 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 72

57
[ 1670-83-3 ]
[ 875305-79-6 ]
3-[(4-tert-butyl-benzyl)-(1H-indole-7-carbonyl)-amino]-propionic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	Example 94; Preparation of 3-[(4-tert-Butyl-benzyl)-(1H-indole-7-carbonyl)-amino]-propionic acid tert-butyl ester 98; 4.37 g (15 mmol) of 3-(4-tert-butyl-benzylamino)-propionic acid tert-butyl ester, 2.42 g (15 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 3.25 g (16.5 mmol) of EDC.HCl were dissolved in 50 ml DCM. The reaction mixture was stirred at rt over night, washed twice with 1N aqueous HCl solution, once with 2N aqueous NaOH solution and once with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated to leave 6.25 g (97%) product as a white solid. MS (ISP) 435.4 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 74-75

58
N'-(4-tert-butyl-benzyl)-N-ethyl-N-m-tolyl-ethane-1,2-diamine [ No CAS ]
[ 1670-83-3 ]
1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(ethyl-m-tolyl-amino)-ethyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	Example 97; Preparation of <strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-[2-(ethyl-m-tolyl-amino)-ethyl]-amide 101; 81 mg (0.50 mol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong>, 162 mg (0.5 mmol) of N'-(4-tert-butyl-benzyl)-N-ethyl-N-m-tolyl-ethane-1,2-diamine and 108 mg (0.55 mmol) of EDC.HCl were dissolved in 5 ml DCM. The reaction mixture was stirred at rt over night. The solvent was evaporated and the residue was dissolved in diethyl ether. The organic layer was washed with 1N aqueous HCl solution, once with 1N aqueous NaOH solution and once with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated to leave 140 mg (55%) product as a colorless oil. MS (ISP) 468.4 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 75

59
[rac]-(4-tert-butyl-benzyl)-(2-hydroxy-2-phenyl-ethyl)-amine [ No CAS ]
[ 1670-83-3 ]
[rac]-1H-indole-7-carboxylic acid (4-tert-butyl-benzyl)-(2-hydroxy-2-phenyl-ethyl)amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 17.08h;	Example 35; Preparation of [rac]-<strong>[1670-83-3]1H-Indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-(2-hydroxy-2-phenyl-ethyl)-amide; To a solution of 100 mg (0.62 mmol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 200 mg of TBTU (0.62 mmol) in 8 ml DMF, were added 0.53 ml (3.1 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 176 mg (0.62 mmol) of [rac]-(4-tert-butyl-benzyl)-(2-hydroxy-2-phenyl-ethyl)-amide were added. After stirring for 17 h at rt, the reaction mixture was diluted with 80 ml water and extracted with EtOAc (2×). The combined organic phases were washed with brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (40 g silica gel; EtOAc/heptane 1:4) to give 181 mg white solid (66%). MS (ISP) 427.4 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 65

60
[ 945717-12-4 ]
[ 1670-83-3 ]
[ 875305-78-5 ]

Yield	Reaction Conditions	Operation in experiment
36%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	Example S67; Preparation of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> (4-tert-butyl-benzyl)-(2-hydroxy-ethyl)-amide; 3.24 g (20 mmol) of 4-tert-butyl benzaldehyde and 1.22 g (20 mmol) of ethanol amine were dissolved in 20 ml methanol and stirred at rt for 30 min. 740 mg (20 mmol) of sodium borohydride were added in portions under nitrogen and the reaction mixture was stirred for 1 h at rt after complete addition. The solvent was evaporated and the residue was dissolved in diethyl ether. The organic layer was washed twice with water, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was dissolved in 20 ml DCM and 3.22 g (20 mol) of 1H-<strong>[1670-83-3]indole-7-carboxylic acid</strong> and 3.82 g (20 mmol) of EDC.HCl were added. The reaction mixture was stirred at rt over night. The solvent was evaporated and the residue was dissolved in EtOAc. The organic layer was washed twice with 1N aqueous HCl solution, once with 2N aqueous NaOH solution and once with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated to leave a colorless oil, which on treatment with diethyl ether yielded 2.54 g (36%) product as a white solid after filtration and drying. MS (ISP) 351.3 (M+H)+.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 36

61
[ 1670-83-3 ]
3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-(cyclopropyl)pyrrolidine [ No CAS ]
1,3-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride [ No CAS ]
[ 289724-90-9 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid; In methanol; dichloromethane; water;	EXAMPLE 11 1-(7-Indolecarbonyl)-3-(R)-(4-(4fluorophenyl)piperidinylmethyl)-4-(S)-(cyclopropyl)pyrrolidine To a solution of 0.02 g (0.067 mmol) of 3-(S)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(S)-(cyclopropyl)pyrrolidine and 0.0012 g of (0.01 mmol) dimethylanrinopyridine (DMAP) in 2 mL of CH2Cl2 at rt was added 0.019 g (0.1 mmol) of 1,3-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) and 0.016 g (0.1 mmol) of <strong>[1670-83-3]7-indolecarboxylic acid</strong> and the reaction mixture was stirred for 1 h. The reaction mixture was partitioned between ethyl acetate and sat'd NaHCO3 solution. The organic fraction was dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chomatography (HPLC Waters Nova-Pak 8*10 RCM 25-40% MeOH in H2O 0.5% TFA) to give the title compound. 1H NMR (CD3OD) d (key peaks) 7.91 (m, 1H), 7.50 (m, 1H), 7.39 (m, 1H), 7.32-7.22 (m, 1H), 7.10-7.01 (m, 3H), 0.82-0.10 (m, 5H); Mass Spectrum (ESI) m/e 446 (M+1).

Reference： [1]Patent: US6362201,2002,B1

62
[ 1670-83-3 ]
BOP-Cl [Bis-(2-oxo-3-oxazolidinyl)phosphinic chloride] [ No CAS ]
3-(SR)-(4-phenylpiperidinylmethyl)-4-(RS)-(thien-3-yl)pyrrolidine [ No CAS ]
1-(7-Indolylcarbonyl)-3-(RS)-(4-phenylpiperidinylmethyl)-4-(RS)-(thien-3-yl)pyrrolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane;	EXAMPLE 12 1-(7-Indolylcarbonyl)-3-(RS)-(4-phenylpiperidinylmethyl)-4-(RS)-(3-thienyl)pyrrolidine To a solution of 0.022 g (0.067 mmol) of 3-(SR)-(4-phenyl piperidinylmethyl)-4-(RS)-(3-thienyl)pyrrolidine and 0.016 g (0.1 mmol) of <strong>[1670-83-3]indole-7-carboxylic acid</strong> in 2 mL of CH2Cl2 and 0.037 mL (0.27 mmol) of triethylamine was added 0.022 g (0.087 mL) of BOP-Cl [Bis-(2-oxo-3-oxazolidinyl)phosphinic chloride] and the reaction mixture was stirred at rt for 5 h. The reaction mixture concentrated and purified by chomatography (silica, acetone: hexanes, 1:3 to 1:2) to give the title compound. 1H NMR (CDCl3) delta; 10.02 (bs, 1H), 7.79 (bs, 1H), 7.02-7.53 (m, 11H), 6.62 (bs, 1H), 4.15-4.19 (m, 2H); Mass Spectrum (CI) m/e=482 (M+1).

Reference： [1]Patent: US6303593,2001,B1

63
[ 1670-83-3 ]
[ 15532-75-9 ]
1-(1H-indol-7-ylcarbonyl)-4-[3(trifuoromethyl)phenyl]piperazine [ No CAS ]
1-(1H-Indole-7-ylcarbonyl)-4-[3-(trifluoromethyl)phenyl]piperazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.14 g (43%); 5.6 g (77%)	With 1,1'-carbonyldiimidazole; In N-methyl-acetamide;	XI. 1-(1H-Indole-7-ylcarbonyl)-4-[3-(trifluoromethyl)phenyl]piperazine To a cooled solution of indole 7-carboxylic acid (3.22 g; 0.02 moles) in 30ml dimethylformamide was added N,N'-carbonyldiimidazole (3.24 g; 0.02 moles). After 45 minutes, a solution of 4-(3-(trifluoromethyl)phenyl)piperazine (5.76 g; 0.025 moles) in 10 ml DMFwas added. This was stirred for 18 hours at ambient temperature. The solvent was then concentrated off and the resulting oil was partitioned between ethyl acetate and water. The aqueous was extracted twice with ethyl acetate and the organics were washed with water and dried (saturatedNaCl, MgSO4). The desired amine was purified via flash chromatography (10% ethyl acetate/dichloromethane), to give 5.6 g (77%) of a solid, m.p. 147-151 C. The solid was recrystallized from methanol to give 3.14 g (43%) of 1-(1H-indol-7-ylcarbonyl)-4-[3(trifuoromethyl)phenyl]piperazine, m.p. 149-151 C. ANALYSIS: Calculated for C20 H18 F3 N3 O: 64.33% C 4.86% H 11.25% N Found: 64.21% C 4.78% H 11.05% N