[ CAS No. 10241-97-1 ] {[proInfo.proName]}

Name: 10241-97-1|5-Methyl-1H-indole-2-carboxylic acid|98%
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SKU: A105309
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Quality Control of [ 10241-97-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 10241-97-1 ]

Product Details of [ 10241-97-1 ]

CAS No. :	10241-97-1	MDL No. :	MFCD00047166
Formula :	C₁₀H₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DAITVOCMWPNFTL-UHFFFAOYSA-N
M.W :	175.18	Pubchem ID :	259188
Synonyms :

Calculated chemistry of [ 10241-97-1 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.1
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	50.22
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) :	-5.47 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.39
Log Po/w (XLOGP3) :	2.67
Log Po/w (WLOGP) :	2.17
Log Po/w (MLOGP) :	1.38
Log Po/w (SILICOS-IT) :	2.34
Consensus Log Po/w :	1.99

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.05
Solubility :	0.155 mg/ml ; 0.000882 mol/l
Class :	Soluble
Log S (Ali) :	-3.44
Solubility :	0.0641 mg/ml ; 0.000366 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.04
Solubility :	0.159 mg/ml ; 0.00091 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.39

Safety of [ 10241-97-1 ]

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

Application In Synthesis of [ 10241-97-1 ]

* 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 [ 10241-97-1 ]
Downstream synthetic route of [ 10241-97-1 ]

[ 10241-97-1 ] Synthesis Path-Upstream 1~2

1
[ 29289-13-2 ]
[ 127-17-3 ]
[ 10241-97-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 24, p. 4385 - 4388

2
[ 91462-34-9 ]
[ 10241-97-1 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1887, vol. 239, p. 227

[ 10241-97-1 ] Synthesis Path-Downstream 1~88

1
[ 91462-34-9 ]
[ 10241-97-1 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1887,vol. 239,p. 227

2
[ 10241-97-1 ]
[ 116247-30-4 ]
[ 116247-34-8 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1988,vol. 27,p. 93 - 95

3
[ 10241-97-1 ]
[ 78-95-5 ]
5-Methyl-1H-indole-2-carboxylic acid 2-oxo-propyl ester [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1992,vol. 31,p. 583 - 589

4
[ 10241-97-1 ]
[ 147539-21-7 ]
1-[5-Methylindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 89 1-[5-Methylindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine (III) Following the general procedure of EXAMPLE 16 and making non-critical variations but starting with <strong>[10241-97-1]5-methylindole-2-carboxylic acid</strong> (0.23 g), 1-[3-(1-methylethylamino)-2-pyridinyl]piperazine (0.29 g) and 1,1'-carbonyldiimidazole (0.21 g) the title compound is obtained, mp 199°-201°.

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 1505 - 1508
[2]Patent: US5489593,1996,A

5
[ 10241-97-1 ]
[ 614-96-0 ]

Reference： [1]Tetrahedron,1995,vol. 51,p. 2091 - 2098

7
[ 10241-97-1 ]
[ 39979-08-3 ]
7-[(5-methyl-1H-indole-2-carbonyl)-amino]-heptanoic acid methyl ester [ No CAS ]

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

8
[ 10241-97-1 ]
7-amino-heptanoic acid benzyloxy-amide [ No CAS ]
5-methyl-1H-indole-2-carboxylic acid (6-benzyloxycarbamoyl-hexyl)-amide [ No CAS ]

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

9
[ 109-01-3 ]
[ 10241-97-1 ]
(5-methyl-1H-indol-2-yl)-(4-methylpiperazin-1-yl)methanone [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 3957 - 3960
[2]Journal of Medicinal Chemistry,2005,vol. 48,p. 8289 - 8298

10
[ 10241-97-1 ]
[ 403860-64-0 ]
5-methyl-1H-indole-2-carboxylic acid (1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl)-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 4385 - 4388

11
[ 29289-13-2 ]
[ 127-17-3 ]
[ 10241-97-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 4385 - 4388

12
[ 10241-97-1 ]
[ 123665-42-9 ]
[ 186430-35-3 ]

Yield	Reaction Conditions	Operation in experiment
		Example 73 5-Methyl-1H-indole-2-carboxylic acid ((1S)-dimethylcarbamoyl-2-phenyl-ethyl)-amide (S)-2-Amino-N,N-dimethyl-3-phenyl-propionamide hydrochloride (1.0 mmol) and <strong>[10241-97-1]5-methyl-1H-indole-2-carboxylic acid</strong> (1.0 mmol) were coupled according to Procedure A (0 - 25 °C reaction temperature). The crude product was triturated with 1:1 ether-hexanes and dried. Yield 302 mg, 87 percent; HPLC (60/40) 5.46 minutes (99 percent); mp 198.5 - 200 °C; PBMS 350 (MH+, 100 percent); Anal. Calcd for C21H23N3O2: C, 72.18; H, 6.63; N, 12.04. Found: C, 72,14; H, 6.90; N, 12.11.

Reference： [1]Patent: EP1134213,2001,A2

13
[ 10241-97-1 ]
5-hydroxy-(1S)-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indole hydrochloride [ No CAS ]
[ 647021-90-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 3815 - 3838

14
[ 67-56-1 ]
[ 10241-97-1 ]
[ 102870-03-1 ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 4511 - 4525
[2]Synlett,2011,p. 521 - 524
[3]Chemistry - A European Journal,2019,vol. 25,p. 4330 - 4334

15
[ 10241-97-1 ]
1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-methyl-1H-indole-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 4511 - 4525

16
[ 10241-97-1 ]
1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-methyl-1H-indole-2-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 4511 - 4525

17
[ 10241-97-1 ]
1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-methyl-1H-indole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 4511 - 4525

18
[ 10241-97-1 ]
7-[(5-methyl-1H-indole-2-carbonyl)-amino]-heptanoyl chloride [ No CAS ]

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

19
[ 10241-97-1 ]
7-[(5-methyl-1H-indole-2-carbonyl)-amino]-heptanoic acid [ No CAS ]

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

20
[ 10241-97-1 ]
5-methyl-1H-indole-2-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

21
[ 10241-97-1 ]
4,6-Dimethyl-9H-pyrano[3,4-b]indol-1-one [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1992,vol. 31,p. 583 - 589

22
[ 10241-97-1 ]
[ 116247-41-7 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1988,vol. 27,p. 93 - 95

23
[ 10241-97-1 ]
[ 102870-03-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium bicarbonate; sulfuric acid; In methanol;	Preparation of Methyl 5-methylindole-2-carboxylate <strong>[10241-97-1]5-Methylindole-2-carboxylic acid</strong> (0.9 g, 5.13 mmol) was dissolved in methanol (25 ml) and treated with sulphuric acid (0.5 ml). The mixture was refluxed for 4 h. The volume of solvent was reduced and the residue treated with sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic fractions were dried and concentrated to give the desired ester.

Reference： [1]Patent: US6403561,2002,B1

24
(+/-)-cis-N-[(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]-1,2-cyclohexanediamine hydrochloride [ No CAS ]
[ 10241-97-1 ]
(+/-)-cis-N₁-[(5-Methylindol-2-yl)carbonyl]-N₂-[(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]-pyridin-2-yl)carbonyl]-1,2-cyclohexanediamine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		[Example 114] (+-)-cis-N1-[(5-Methylindol-2-yl)carbonyl]-N2-[(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]-pyridin-2-yl)carbonyl]-1,2-cyclohexanediamine hydrochloride: The title compound was obtained from (+-)-cis-N-[(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]-1,2-cyclohexanediamine hydrochloride and <strong>[10241-97-1]5-methylindole-2-carboxylic acid</strong> in a similar manner to Example 6. 1H-NMR (DMSO-d6) delta: 1.35-1.50(2H,m), 1.50-1.80(4H,m), 1.85-2.07(2H,m), 2.36(3H,s),2.88(3H,s), 3.12(2H,br.s), 3.53(2H,br.s), 4.15-4.30(2H,m), 4.30-4.80(2H,br), 7.00(1H,dd,J=8.4,1.5Hz), 7.05(1H,d,J=1.5Hz)1 7.30(1H,d,J=8.4Hz), 7.38(1H,s), 8.00(1H,d,J=7.3Hz), 8.43(1H,br.s), 11.45(1H,br.s), 11.49(1H,br.s). MS (FAB) m/z: 452(M+H)+.

Reference： [1]Patent: EP1270557,2003,A1

Yield	Reaction Conditions	Operation in experiment
		(3) 5-Methyl-2-indolecarboxylic acid: 1H NMR (DMSO-d6) delta: 2.36 (3H, s), 6.98 (1H, dd, J=1.0, 2.0 Hz), 7.04-7.08 (1H, m), 7.30-7.33 (1H, m), 7.40 (1H, s), 11.6 (1H, br-s), 12.9 (1H, br-s).

26
[ 10241-97-1 ]
[ 43115-40-8 ]
[ 783370-02-5 ]

Yield	Reaction Conditions	Operation in experiment
15%	With triethanolamine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In N,N-dimethyl-formamide;	EXAMPLE 48 5-Methyl-1H-indole-2-carboxylic acid-(5-ethanesulfonyl-2-hydroxy-phenyl)-amide TEA (0.28 mL, 2.0 mmole) was added to a solution of <strong>[10241-97-1]5-methyl-1H-indole-2-carboxylic acid</strong> (175 mg, 1.0 mmole), 2-amino-4-ethanesulfonyl-phenol (201 mg, 1.0 mmole), and BOP (442 mg, 1.0 mmole) in DMF (2.0 mL). The reaction mixture was shaken at room temperature overnight and then diluted with 1N hydrochloric acid (20 mL). The resulting precipitate was filtered off and washed with water. The residue was triturated with EtOAc (40 mL), the solvent was dried over magnesium sulfate, filtered, and reduced in volume while slowly adding hexanes until crystallization began. The crystalline product was filtered off and air-dried to afford the title compound as a brown powder (55 mg, 15percent yield). AP-/MS=359; AP-/MS=357.

Reference： [1]Patent: US2004/220229,2004,A1

27
2-methyl-1-(piperidin-4-yl)-2-propanol [ No CAS ]
[ 10241-97-1 ]
[ 1126084-35-2 ]

Yield	Reaction Conditions	Operation in experiment
71%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20℃;	General procedure: To a solution of <strong>[10241-97-1]5-methyl-1H-indole-2-carboxylic acid</strong> (20) (263mg, 1.50mmol) in THF (7mL) were added 2-(piperidin-4-yl)ethanol (213mg, 1.65mmol), 1-hydroxybenzotriazole (HOBt, 101mg, 0.750mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDAC) hydrochloride (316mg, 1.65mmol), followed by stirring at room temperature for 14h. The reaction mixture was partitioned between ethyl acetate and 0.5M aqueous hydrochloric acid. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated in vacuo. The residue was recrystallized from ethyl acetate/acetonitrile (5mL/2mL) to give 3 (365mg, 85.0percent) as a beige powder.
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃;	Example 24 To a solution of 1800 mg of <strong>[10241-97-1]5-methylindole-2-carboxylic acid</strong> and 1500 mg of 2-methyl-1-(piperidin-4-yl)-2-propanol in 25 mL of DMF were added 2100 mg of 1-ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride and 1500 mg of 1-hydroxybenzotriazole, followed by stirring at room temperature for 1 day. 0.5M aqueous hydrochloric acid was added to the reaction liquid, followed by extraction with ethyl acetate. The organic layer was washed with 0.5M aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography [chloroform:methanol = 1:0-10:1], and then crystallized from a mixture of ethyl acetate/diisopropyl ether to obtain 2140 mg of 2-methyl-1-{1-[(5-methyl-1H-indol-2-yl)carbonyl]piperidin-4-yl}propan-2-ol as a white crystal.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 5261 - 5270
[2]Patent: EP2181990,2010,A1 .Location in patent: Page/Page column 15

28
[ 10241-97-1 ]
(S)-8-Chloromethyl-4-hydroxy-3,6,7,8-tetrahydro-pyrrolo[3,2-e]indole-2-carboxylic acid methyl ester; hydrochloride [ No CAS ]
[ 1228694-06-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2722 - 2725
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2722 - 2725

29
[ 35161-71-8 ]
[ 10241-97-1 ]
[ 1250829-38-9 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 6923 - 6932

30
[ 10241-97-1 ]
[ 698-19-1 ]
[ 1263788-01-7 ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 541 - 543

31
[ 10241-97-1 ]
[ 698-19-1 ]
[ 1263788-26-6 ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 541 - 543

32
[ 10241-97-1 ]
[ 113258-86-9 ]
[ 1263787-87-6 ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 541 - 543

33
[ 10241-97-1 ]
[ 113258-86-9 ]
[ 1263788-01-7 ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 541 - 543

34
[ 10241-97-1 ]
[ 1278517-82-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 1550 - 1561

35
[ 10241-97-1 ]
[ 95538-31-1 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; for 0.25h;Reflux; Inert atmosphere;	General procedure: Commercial indole-2-carboxylic acid was dissolved in thionyl chloride (1.5 mL/mmol) and the suspension was boiled for 15 min, during which time typically a dark green solution was formed. Excess thionyl chloride was removed under reduced pressure and the solid residue was suspended in toluene and the suspension was evaporated to dryness (toluene treatment was repeated three times). The green-grayish solid residues were used without further purification.
	With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20℃;	A vial was charged with 5-methyl-lH-indole-2-carboxylic acid (175 mg, 1.00 mmol, 1.00 equiv), DCM (10 mL) and oxalyl chloride (381 mg, 3.00 mmol, 3.00 equiv). N,N- Dimethylformamide (0.05 mL) was added at 0 °C. The resulting solution was stirred for 4 h at room temperature and concentrated under reduced pressure to provide 194 mg (crude) of 5- methyl-lH-indole-2-carbonyl chloride

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 1550 - 1561
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 892 - 913
[3]Patent: WO2019/46318,2019,A1 .Location in patent: Paragraph 00230
[4]Journal of Organic Chemistry,2019,vol. 84,p. 5886 - 5892

36
[ 10241-97-1 ]
[ 943117-52-0 ]