26807-73-8|1-Benzyl-1H-indol-5-amine| Ambeed

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Structure of 26807-73-8

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Quality Control of [ 26807-73-8 ] Purity: 97% SDS Specification

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Product Details of [ 26807-73-8 ]

CAS No. :	26807-73-8
Formula :	C₁₅H₁₄N₂
M.W :	222.29
SMILES Code :	NC1=CC2=C(N(CC3=CC=CC=C3)C=C2)C=C1
MDL No. :	MFCD03070173
InChI Key :	UYDNPZLYDODKKA-UHFFFAOYSA-N
Pubchem ID :	2794624

Safety of [ 26807-73-8 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H318
Precautionary Statements:	P280-P305+P351+P338
Class:	8
UN#:	3259
Packing Group:	Ⅲ

Computational Chemistry of [ 26807-73-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	17
Num. arom. heavy atoms	15
Fraction Csp3	0.07
Num. rotatable bonds	2
Num. H-bond acceptors	0.0
Num. H-bond donors	1.0
Molar Refractivity	72.09
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	30.95 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.25
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	-2.79
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.28
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.66
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.69
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.62

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	0.02
Solubility	232.0 mg/ml ; 1.04 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Highly soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	2.69
Solubility	110000.0 mg/ml ; 494.0 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Highly soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-5.03
Solubility	0.00208 mg/ml ; 0.00000938 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	Yes
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-9.64 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	1.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.52

Application In Synthesis of [ 26807-73-8 ]

* 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.

Downstream synthetic route of [ 26807-73-8 ]

[ 26807-73-8 ] Synthesis Path-Downstream 1~35

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid; In dichloromethane; at 20℃;	General procedure: To a reaction flask were added 2-chloro-4-tert-butylcarbonylamino-phenol (24.35 g, 100 mmol), 2-chloromethylpyridine hydrochloride (32.8 g, 200 mmol), potassium carbonate (41.4 g, 300 mmol) and tetrabutyl amimonium iodide (1.107 g, 3 mmol). To the flask was added DMF (100ml). The reaction mixture was stirred. After the reaction finished, the reaction solution was poured into water (1 L). The mixture was extracted with ethyl acetate three times. The ethyl acetate layers were combined. The resultant organic layer was washed with water (500 ml) and staturated saline solution (500 ml), successively. The resulting mixture was dried over anhydrous magnesium sulfate for 30 min, filtered and rotary-evaporated to dryness. The resultant substance was purified with column chromatography (eluent: ethyl acetate:petroleum ether = 1:) to give N-(3-chloro-4-(pyridin-2-yl-methoxy)phenyl)-tert-butoxyacylamine.; To a reaction flask was added N-(3-chloro-4-(pyridin-2-yl-methoxy) phenyl)-tert-butoxyacylamine. N-(3-chloro-4-(pyridin-2-yl-methoxy)phenyl)-tert-butoxy acylamine was dissolved with 20% TFA in DCM (50 ml). The mixture was stirred at the room temperature. After the reaction finished, the solvent was rotary-evaporated. The residue was dissolved in DCM (200 ml). The resulting solution was washed with saturated sodium carbonate three times (200 ml×3), with water (200 ml) once, with saturated saline solution (200 ml) once, successively. The resultant substance was dried over anhydrous magnesium sulfate and filtered. The solvent was rotary-evaporated to give the target product.

2
[ 26807-73-8 ]
[ 171178-48-6 ]
[ 202272-97-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1401 - 1405.

3
[ 26807-73-8 ]
[ 189680-99-7 ]
N₄-(1-Benzyl-1H-indol-5-yl)-N₆,N₆-dimethyl-pyrido[3,4-d]pyrimidine-4,6-diamine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 1401 - 1405.

4
[ 26807-73-8 ]
4-chloro-5-[3-methyl-5-(morpholine-4-carbonyl)-1H-pyrrol-2-ylmethylene]-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one [ No CAS ]
4-(1-benzyl-1H-indol-5-ylamino)-5-[3-methyl-5-(morpholine-4-carbonyl)-1H-pyrrol-2-ylmethylene]-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one [ No CAS ]

References: [1]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 2153 - 2157.

5
[ 26807-73-8 ]
5-(4-chloro-6-oxo-6,7-dihydro-pyrrolo[2,3-d]pyrimidin-5-ylidenemethyl)-4-methyl-1H-pyrrole-2-carboxylic acid (2-morpholin-4-yl-ethyl)-amide [ No CAS ]
5-[4-(1-benzyl-1H-indol-5-ylamino)-6-oxo-6,7-dihydro-pyrrolo[2,3-d]pyrimidin-5-ylidenemethyl]-4-methyl-1H-pyrrole-2-carboxylic acid (2-morpholin-4-yl-ethyl)-amide [ No CAS ]

References: [1]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 2153 - 2157.

6
[ 65795-95-1 ]
[ 26807-73-8 ]

Yield	Reaction Conditions	Operation in experiment
63%	With iron; acetic acid; In methanol; at 65℃; for 2.0h;	1-benzyl-5-nitro-1H-indole (500 mg, 1.98 mmol, 1.0 equiv.), reducing iron powder (555 mg,9.9 mmol, 5.0 equiv.) dissolved in an appropriate amount of MeOH, and added with stirring AcOH (594 mg, 9.9 mmol, 5.0 equiv.) at 65Stir at C for 2 hours. The TLC monitors the reaction in real time. After the reaction, the reaction solution was filtered through celite, washed with methanol, and distilled under reduced pressure.The crude product was purified by silica gel column chromatography toield of 1-benzyl-1H-indole-5-amine (280 mg, yield: 63%).
22.4 g	With water; iron; ammonium chloride; In ethanol; at 70 - 75℃; for 3.5h;Reflux;	[Reference Example 12] (0454) (0455) To the mixture of 45.5 g of 1-benzyl-5-nitro-1H-indole, 6.15 g of ammonium chloride, 360 mL of ethanol and 90 mL of water, 35.2 g of iron powder was added in portions at an external temperature of 70 to 75C, and the resultant was heated at reflux for three hours and 30 minutes. After cooling the reaction mixture to room temperature, water and ethyl acetate were added thereto, and the insoluble matter was filtered off. The filter cake was washed with water and ethyl acetate. The filtrate and the washings were combined, the organic layer was separated, sequentially washed with water and a saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Diisopropyl ether and ethyl acetate were added to the obtained residue and the solid was collected by filtration. The obtained solid was purified by silica gel column chromatography (gradient elution with hexane:ethyl acetate = 90:10-50:50), and hexane was added to the thus obtained residue, and the solid was collected by filtration to give 22.4 g of 1-benzyl-1H-indol-5-amine as a pale brown solid. 1H-NMR (DMSO-d6) delta: 4.47 (2H, s), 5.27 (2H, s), 6.17 (1H, d, J = 2.6 Hz), 6.47 (1H, dd, J = 8.6, 2.0 Hz), 6.68 (1H, d, J = 2.0 Hz), 7.08 (1H, d, J = 8.6 Hz), 7.12-7.17 (2H, m), 7.21-7.32 (4H, m).

References: [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 3537 - 3549.
[2]Chemical Communications,2012,vol. 48,p. 7982 - 7984.
[3]Patent: CN109232358,2019,A .Location in patent: Paragraph 0159; 0164-0165.
[4]Journal of Medicinal Chemistry,2005,vol. 48,p. 1107 - 1131.
[5]Archiv der Pharmazie,2005,vol. 338,p. 67 - 73.
[6]Journal of Medicinal Chemistry,2007,vol. 50,p. 5509 - 5513.
[7]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1332 - 1336.
[8]Patent: EP2915804,2015,A1 .Location in patent: Paragraph 0454-0455.

7
[ 26807-73-8 ]
[ 214476-09-2 ]
4-(1-benzyl-1H-indol-5-ylamino)-7-ethoxy-6-nitro-quinoline-3-carbonitrile [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1107 - 1131.

8
[ 26807-73-8 ]
[ 1077-28-7 ]
5-[1,2]dithiolan-3-yl-pentanoic acid (1-benzyl-1H-indol-5-yl)-amide [ No CAS ]

References: [1]Archiv der Pharmazie,2005,vol. 338,p. 67 - 73.

9
[ 26807-73-8 ]
[ 104224-50-2 ]
5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid (1-benzyl-1H-indol-5-yl)-amide [ No CAS ]

References: [1]Archiv der Pharmazie,2006,vol. 339,p. 193 - 200.

10
[ 94-02-0 ]
[ 26807-73-8 ]
ethyl 3-phenyl-3-(1-benzyl-1H-indole-5-ylamino)-acrylate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5509 - 5513.

11
[ 6146-52-7 ]
[ 26807-73-8 ]

References: [1]Archiv der Pharmazie,2005,vol. 338,p. 67 - 73.
[2]Journal of Medicinal Chemistry,2005,vol. 48,p. 1107 - 1131.
[3]Patent: EP2915804,2015,A1 .
[4]Patent: CN109232358,2019,A .

12
[ 100-39-0 ]
(1R,2R)-O-Merrifield bound N-(2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-2'-phenylacetamide [ No CAS ]
[ 26807-73-8 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1107 - 1131.

13
[ 26807-73-8 ]
[ 848133-58-4 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1107 - 1131.

14
[ 26807-73-8 ]
4-dimethylamino-but-2-enoic acid [4-(1-benzyl-1H-indol-5-ylamino)-3-cyano-7-ethoxy-quinolin-6-yl]-amide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1107 - 1131.

15
5-(4-chloro-6-oxo-6,7-dihydro-pyrrolo[2,3-d]pyrimidin-5-ylidenemethyl)-1H-pyrrole-2-carboxylic acid (2-morpholin-4-yl-ethyl)-amide [ No CAS ]
[ 111-96-6 ]
[ 26807-73-8 ]
[ 346599-73-3 ]

Yield	Reaction Conditions	Operation in experiment
13.5 mg (42%)	With toluene-4-sulfonic acid; In hydrogenchloride; 1-methyl-2-pyrrodinone;	EXAMPLE 12 SYNTHESIS OF 5-[4-(1-BENZYL-1H-INDOL-5-YLAMINO)-6-OXO-6,7-DIHYDRO-PYRROLO [2,3-D]PYRIMIDIN-5-YLIDENEMETHYL]-1H-PYRROLE-2-CARBOXYLIC ACID (2-MORPHOLIN-4-YL-ETHYL)-AMIDE HYDROCHLORIDE (FORMULA 12) A mixture of 5-(4-chloro-6-oxo-6,7-dihydro-pyrrolo[2,3-d]pyrimidin-5-ylidenemethyl)-1H-pyrrole-2-carboxylic acid (2-morpholin-4-yl-ethyl)-amide, 1 -benzyl-1H-indol-5-ylamine and p-toluenesulfonic acid (5 mg) in 2 mL of 1-methyl-2-pyrrodinone and 2-methoxyethyl ether (1:3) was heated at 170-185 C. for 7 to 15 hours. The reaction mixture was evaporated to dryness and purified by reversed phase HPLC, then dissolved in 2N HCl and acetonitrile and freeze-dried to give 13.5 mg (42%) of the title compound. MS 589.3 [M++1].

References: [1]Patent: US2002/183319,2002,A1 .

16
[ 26807-73-8 ]
1-(1-Benzyl-1H-indol-5-yl)-3quinolin-4-ylurea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		4. 1-(1-Benzyl-1H-indol-5-yl)-3quinolin-4-ylurea From D4 (0.245 g) and <strong>[26807-73-8]5-amino-1-benzyl-(1H)-indole</strong> D6(C) (0.37 g) the title compound (0.25 g), after column chromatography (silica gel, hexane?ethyl acetate) and trituration with diethyl ether, was prepared according to Example 1, Method 2. 1H NMR delta: 5.41 (2H, s), 7.11-7.42 (8H, m), 7.51 (1H, d), 7.64-7.82 (3H, m), 7.98 (1H, d), 8.21 -8.27 (2H, m), 8.71 (1H, d), 9.14 (1H, bs), 9.23 (1H, bs). m/z (API+): 393 (MH+).

References: [1]Patent: US6410529,2002,B1 .

17
[ 77421-13-7 ]
[ 26807-73-8 ]
[ 1026754-66-4 ]

References: [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 3537 - 3549.

18
[ 673-32-5 ]
[ 119072-55-8 ]
[ 26807-73-8 ]
C₂₉H₃₂N₄ [ No CAS ]

References: [1]Organic Letters,2009,vol. 11,p. 4720 - 4723.

19
[ 1234472-68-4 ]
[ 26807-73-8 ]
C₅₀H₅₂FN₅O₆ [ No CAS ]

References: [1]Amino Acids,2010,vol. 38,p. 985 - 990.

20
[ 673-32-5 ]
[ 119072-55-8 ]
[ 26807-73-8 ]
C₂₉H₃₁N₃ [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 1811 - 1822.

21
[ 26807-73-8 ]
[ 1629161-00-7 ]

References: [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 1811 - 1822.

22
methyl 3-chloro-6-cyclopropylpicolinate [ No CAS ]
[ 26807-73-8 ]
methyl 3-((1-benzyl-1H-indol-5-yl)amino)-6-cyclopropylpicolinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 180℃; for 1.0h;Microwave irradiation;	[Example 209] (1259) (1260) The mixture of 221 mg of methyl 3-chloro-6-cyclopropylpicolinate, 253 mg of <strong>[26807-73-8]1-benzyl-1H-indol-5-amine</strong>, 19 mg of tris(dibenzylideneacetone)dipalladium(0), 36 mg of 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene, 710 mg of cesium carbonate, and 15 mL of dioxane, was stirred at 180C for one hour using microwave equipment. After cooling the reaction mixture to room temperature, the insoluble matter was filtered off and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (gradient elution with hexane:ethyl acetate = 95:5-67:33) to give methyl 3-((1-benzyl-1H-indol-5-yl)amino)-6-cyclopropylpicolinate. MS (ESI, m/z): 398 (M+H)+.

References: [1]Patent: EP2915804,2015,A1 .Location in patent: Paragraph 1259-1260.

23
[ 702640-96-8 ]
[ 26807-73-8 ]
methyl 2-((1-benzyl-1H-indol-5-yl)amino)-5-cyclopropylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.3 g	With tris-(dibenzylideneacetone)dipalladium(0); tert-butyl 5-bromo-2-chloroisonicotinate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; for 3.0h;Reflux; Inert atmosphere; Sealed tube;	[Example 93] (1023) (1024) The mixture of 245 mg of <strong>[26807-73-8]1-benzyl-1H-indol-5-amine</strong>, 0.28 g of methyl 2-bromo-5-cyclopropylbenzoate, 50 mg of tris(dibenzylideneacetone)dipalladium(0), 64 mg of 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene, 0.72 g of cesium carbonate, and 3 mL of toluene, was heated at reflux in a sealed tube for three hours under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and ethyl acetate and water were then added thereto. The organic layer was separated, sequentially washed with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (gradient elution with hexane:ethyl acetate = 90:10-80:20) to give 0.3 g of methyl 2-((1-benzyl-1H-indol-5-yl)amino)-5-cyclopropylbenzoate as a yellow oil. 1H-NMR (CDCl3) delta: 0.55-0.63 (2H, m), 0.81-0.90 (2H, m), 1.75-1.86 (1H, m), 3.90 (3H, s), 5.32 (2H, s), 6.49 (1H, d, J = 3.3 Hz), 6.92-7.07 (3H, m), 7.10-7.17 (3H, m), 7.21-7.36 (4H, m), 7.49 (1H, d, J = 2.0 Hz), 7.68 (1H, d, J = 2.0 Hz), 9.20 (1H, s).

References: [1]Patent: EP2915804,2015,A1 .Location in patent: Paragraph 1023-1024.

24
methyl 2-iodo-5-isopropylbenzoate [ No CAS ]
[ 26807-73-8 ]
methyl 2-((1-benzyl-1H-indol-5-yl)amino)-5-isopropylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
122 mg	With tris-(dibenzylideneacetone)dipalladium(0); tert-butyl 5-amino-1-benzyl-1H-indole-2-carboxylate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; for 3.16667h;Reflux; Inert atmosphere;	[Example 113] (1065) (1066) The mixture of 80 mg of <strong>[26807-73-8]1-benzyl-1H-indol-5-amine</strong>, 100 mg of methyl 2-iodo-5-isopropylbenzoate, 15 mg of tris(dibenzylideneacetone)dipalladium(0), 19 mg of 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene, 214 mg of cesium carbonate, and 2 mL of toluene, was heated at reflux for three hours and 10 minutes under a nitrogen atmosphere. The insoluble matter was filtered off and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (gradient elution with hexane:ethyl acetate = 100:0-80:20) to give 122 mg of methyl 2-((1-benzyl-1H-indol-5-yl)amino)-5-isopropylbenzoate as a yellow oil. MS (ESI, m/z): 399 (N4+H)+.

References: [1]Patent: EP2915804,2015,A1 .Location in patent: Paragraph 1065-1066.

25
[ 26807-73-8 ]
[ 90971-88-3 ]
methyl 2-((1-benzyl-1H-indol-5-yl)amino)-5-methylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; at 190℃; for 1.5h;	[Example 205] (1250) (1251) To the solution of 108 mg of 2-bromo-5-methylbenzoic acid in 10 mL of methanol, 0.5 mL of concentrated sulfuric acid was added, and the resultant was heated at reflux for three hours. The reaction mixture was cooled to room temperature, and a saturated aqueous sodium bicarbonate solution and ethyl acetate were then added thereto. The organic layer was separated and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to give methyl 2-bromo-5-methylbenzoate. (1252) To the obtained methyl 2-bromo-5-methylbenzoate, 110 mg of <strong>[26807-73-8]1-benzyl-1H-indol-5-amine</strong>, 10 mg of tris(dibenzylideneacetone)dipalladium(0), 18 mg of 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene, 342 mg of cesium carbonate and 4 mL of toluene were added, and the resultant was stirred at 190C for one hour and 30 minutes using microwave equipment. After cooling the reaction mixture to room temperature, the insoluble matter was filtered off and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (gradient elution with hexane:ethyl acetate = 100:0-75:25) to give methyl 2-((1-benzyl-1H-indol-5-yl)amino)-5-methylbenzoate as a yellow oil. MS (ESI, m/z): 371 (M+H)+.

References: [1]Patent: EP2915804,2015,A1 .Location in patent: Paragraph 1250-1252.

26
methyl 2-chloro-5-cyclopentylnicotinate [ No CAS ]
[ 26807-73-8 ]
methyl 2-((1-benzyl-1H-indol-5-yl)amino)-5-cyclopentylnicotinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
132 mg	With tris-(dibenzylideneacetone)dipalladium(0); tert-butyl 5-amino-1-benzyl-1H-indole-2-carboxylate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In acetic acid butyl ester; for 4.08333h;Reflux; Inert atmosphere;	[Example 127] (1093) (1094) The mixture of 100 mg of <strong>[26807-73-8]1-benzyl-1H-indol-5-amine</strong>, 103 mg of methyl 2-chloro-5-cyclopentylnicotinate, 20 mg of tris(dibenzylideneacetone)dipalladium(0), 25 mg of 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene, 280 mg of cesium carbonate, and 1 mL of butyl acetate, was heated at reflux for four hours and five minutes under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and ethyl acetate and water were then added thereto. The organic layer was separated, washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (gradient elution with hexane:ethyl acetate = 100:0-30:70). Diisopropyl ether was added to the thus obtained residue, and the solid was collected by filtration to give 132 mg of methyl 2-((1-benzyl-1H-indol-5-yl)amino)-5-cyclopentylnicotinate as a yellow solid. 1H-NMR (DMSO-d6) delta: 1.41-1.82 (6H, m), 1.95-2.05 (2H, m), 2.86-2.99 (1H, m), 3.89 (3H, s), 5.40 (2H, s), 6.44 (1H, d, J = 2.6 Hz), 7.15-7.39 (7H, m), 7.48 (1H, d, J = 3.3 Hz), 7.96 (1H, d, J = 2.0 Hz), 8.06 (1H, d, J = 2.6 Hz), 8.28 (1H, d, J = 2.6 Hz), 9.84 (1H, s). MS (ESI, m/z): 426 (M+H)+, 424 (M-H)-.

References: [1]Patent: EP2915804,2015,A1 .Location in patent: Paragraph 1093-1094.

27
methyl 2-chloro-5-cyclopentylnicotinate [ No CAS ]
[ 26807-73-8 ]
2-((1-benzyl-1H-indol-5-yl)amino)-5-cyclopentylnicotinic acid [ No CAS ]