[ CAS No. 882679-96-1 ] {[proInfo.proName]}

Name: 882679-96-1|Methyl 4-bromo-1H-indole-6-carboxylate|97%
Brand: Ambeed
SKU: A101336
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Quality Control of [ 882679-96-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 882679-96-1 ]

Product Details of [ 882679-96-1 ]

CAS No. :	882679-96-1	MDL No. :	MFCD03867040
Formula :	C₁₀H₈BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BHADJPVQZXGIFH-UHFFFAOYSA-N
M.W :	254.08	Pubchem ID :	24728007
Synonyms :

Calculated chemistry of [ 882679-96-1 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.1
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	57.28
TPSA :	42.09 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) :	-6.01 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.19
Log Po/w (XLOGP3) :	2.59
Log Po/w (WLOGP) :	2.72
Log Po/w (MLOGP) :	2.08
Log Po/w (SILICOS-IT) :	3.02
Consensus Log Po/w :	2.52

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.39
Solubility :	0.103 mg/ml ; 0.000407 mol/l
Class :	Soluble
Log S (Ali) :	-3.12
Solubility :	0.192 mg/ml ; 0.000754 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.22
Solubility :	0.0155 mg/ml ; 0.0000608 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.78

Safety of [ 882679-96-1 ]

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

Application In Synthesis of [ 882679-96-1 ]

* 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 [ 882679-96-1 ]
Downstream synthetic route of [ 882679-96-1 ]

[ 882679-96-1 ] Synthesis Path-Upstream 1~1

1
[ 223519-08-2 ]
[ 882679-96-1 ]

Reference： [1] Patent: WO2015/104677, 2015, A1,

[ 882679-96-1 ] Synthesis Path-Downstream 1~55

1
[ 882679-96-1 ]
[ 374633-27-9 ]

Yield	Reaction Conditions	Operation in experiment
		A solution of sodium hydroxide (14.08 g, 352.1 mmol) in water (100 niL) was added a to a solution of 4-bromo-lH-indole-6-carboxylic acid methyl ester in methanol (14.91 niL, 58.7 mmol) at room temperature and stirred for 2.5 hours. The reaction mixture was concentrated in vacuo, IN HCl was added, and the product was extracted with ethyl acetate to give 13.0 g of 4-bromo-lH-indole-6-carboxylic acid, which was used in the next step with no further purification. 1H NMR (400 MHz, CD3OD) 5 8.13 (t, J= 1.0 Hz, IH), 7.87 (d, J= 1.3 Hz, IH), 7.53 (t, /= 3.4 Hz, IH), 8.13 (d, / = 4.2 Hz5IH) .

Reference： [1]Patent: WO2006/101937,2006,A1 .Location in patent: Page/Page column 39

2
[ 882679-96-1 ]
[ 1101818-09-0 ]
[ 1426154-37-1 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 2125 - 2138

3
(E)-methyl 3-bromo-4-(2-(dimethylamino)vinyl)-5-nitrobenzoate [ No CAS ]
[ 882679-96-1 ]

Yield	Reaction Conditions	Operation in experiment
67%	With iron; acetic acid; at 50 - 90℃; for 2h;	To a solution of (E)-methyl 3-bromo-4-(2-(dimethylamino)vinyl)-5-nitrobenzoate (1-21, 3.1 g, 9.42 mmol) in acetic acid (2 mL) was added iron (2.104 g, 37.7 mmol) at 50 C and the reaction mixture was stirred at 85-90 C for 2 h. After completion of reaction, cooled to RT, filtered through celite, residue washed with ethyl acetate and organic layer was washed with water and mother liquor was concentrated which was further purified by column chromatography (silica gel, 20-30% ethyl acetate in pet ether) to obtain the title compound. Yield: 1.6 g (67 %); JH NMR (DMSO-de; 300 MHz): 6 11.90 (s, 1H), 7.76 (s, 1H), 7.73 (t, J= 4.8 Hz, 1H), 6.49 (sz, 1H), 3.87 (s, 3H); MS (ESI+): m/z 223.9.

Reference： [1]Patent: WO2015/104677,2015,A1 .Location in patent: Page/Page column 60-61

4
[ 882679-96-1 ]
4-bromo-1-ethyl-N-((6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl)methyl)-1H-indole-6-carboxamide [ No CAS ]

Reference： [1]Patent: WO2015/104677,2015,A1

5
[ 882679-96-1 ]
1-ethyl-N-((6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl)methyl)-4-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-indole-6-carboxamide [ No CAS ]

Reference： [1]Patent: WO2015/104677,2015,A1

6
[ 882679-96-1 ]
4-bromo-1-ethyl-1H-indole-6-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2015/104677,2015,A1

7
[ 882679-96-1 ]
[ 75-03-6 ]
methyl 4-bromo-1-ethyl-1H-indole-6-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%		To a solution of methyl 4-bromo-lH-indole-6-carboxylate (1-22, 800 mg, 3.15 mmol) in DMF (8 mL) was added NaH (126 mg, 3.15 mmol) and the reaction mixture was stirred at RT for 5 minutes and added ethyl iodide (0.382 mL, 4.72 mmol) and stirred at RT for 0.5 h. After completion of reaction, water was added and extracted with ethyl acetate. The organic layer was washed with water and concentrated which was further purified by column chromatography (silica gel, 5-10 % ethyl acetate in pet ether) to obtain the title compound. Yield: 511 mg (57 %); JH NMR (DMSO-d6; 300 MHz): 68.08 (s, 1H), 7.98 (s, 1H), 7.34 (d, J= 3 Hz, 1H), 6.60 (d, J = 3 Hz, 1H), 4.27 (q, J= 7.5 Hz, 2H), 3.96 (s, 3H), 1.50 (t, J= 7.5 Hz, 3H); MS (ESI+): m/z 203.

Reference： [1]Patent: WO2015/104677,2015,A1 .Location in patent: Page/Page column 61

8
[ 223519-08-2 ]
[ 882679-96-1 ]

Reference： [1]Patent: WO2015/104677,2015,A1

9
[ 882679-96-1 ]
methyl 4-bromoindoline-6-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.75 g	With triethylsilane; trifluoroacetic acid; at 60℃; for 0.75h;	Step a. To a solution of methyl 4-bromo-lH-indole-6-carboxylate (CAS Number 882679-96-1) (1.0 g, 3.95 mmol) in TFA (5 ml) was added triethylsilane (1.9 ml, 11.86 mmol) at rt. The reaction mixture was stirred at 60C for 45 min. The resulting reaction mixture was cooled to rt, poured into saturated NaHC03 solution (50 ml) extracted with EtOAc (3 x 30 ml). The combined organic layer was dried over Na2S04, filtered and concentrated under reduced pressure. The resulting residue was purified by flash chromatography (10% EtOAc in hexane) yielding methyl 4-bromoindoline-6-carboxylate (0.75 g, 29.4 mmol). LCMS: Method C, 2.31 min, MS: ES+ 256.3, 258.3; NMR (400 MHz, DMSO-d6) delta ppm 7.20 (d, J= 1.2 Hz, 1H), 6.94 (d, J=1.6 Hz, 1H), 6.19 (s, 1H), 3.80 (s, 3H), 3.54 (t, J=8.8 Hz, 2H), 2.97 (t, J=8.8 Hz, 2H).
2.40 g	With triethylsilane; trifluoroacetic acid; at 60℃; for 1h;	Step a. To a solution of <strong>[882679-96-1]methyl 4-bromo-1H-indole-6-carboxylate</strong> (CAS Number 882679-96-1; 3.000 g, 11.86 mmol) in TFA (14 ml) was added triethylsilane (4.13 g, 35.6 mmol) dropwise at rt. The reaction mixture was heated at 60C for 1 h. The resulting mixture was evaporated under vacuum. The resulting residue was diluted with saturated NaHCO3 solution (150 ml) and extracted with EtOAc (2 x 100 ml). The combined organic phase was washed with brine solution (75 ml), dried over Na2SO4, filtered and concentrated under reduced pressure to yielding methyl 4-bromoindoline-6-carboxylate as thick yellow oil (2.40 g, 9.37 mmol). This material was used directly in next step without further purification. LCMS:Method C, 2.209 mi MS: ES+ 256.21; 258.21

Reference： [1]Patent: WO2017/9650,2017,A1 .Location in patent: Page/Page column 90
[2]Patent: WO2017/141036,2017,A1 .Location in patent: Page/Page column 89; 90

10
[ 882679-96-1 ]
methyl 4-bromo-1-((tert-butoxycarbonyl)-L-prolyl)indoline-6-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/9650,2017,A1

11
[ 882679-96-1 ]
methyl 1-((tert-butoxycarbonyl)-L-prolyl)-4-phenylindoline-6-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/9650,2017,A1

12
[ 882679-96-1 ]
1-((tert-butoxycarbonyl)-L-prolyl)-4-phenylindoline-6-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2017/9650,2017,A1

13
[ 882679-96-1 ]
tert-butyl (S)-2-(6-carbamoyl-4-phenylindoline-1-carbonyl)pyrrolidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/9650,2017,A1

14
[ 882679-96-1 ]
tert-butyl (S)-2-(6-(hydroxymethyl)-4-phenylindoline-1-carbonyl)pyrrolidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/9650,2017,A1

15
[ 882679-96-1 ]
tert-butyl (S)-2-(6-formyl-4-phenylindoline-1-carbonyl) pyrrolidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/9650,2017,A1

16
[ 882679-96-1 ]
tert-butyl (S)-2-(6-(1H-imidazol-2-yl)-4-phenylindoline-1-carbonyl)pyrrolidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/9650,2017,A1

17
[ 882679-96-1 ]
tert-butyl (S)-2-(4-phenyl-6-(4H-1,2,4-triazol-3-yl)indoline-1-carbonyl)pyrrolidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/9650,2017,A1

18
[ 882679-96-1 ]
[ 74-88-4 ]
methyl 4-bromo-1-methyl-1H-indole-6-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20℃; for 3h;	To a mixture of <strong>[882679-96-1]methyl 4-bromoindole-6-carboxylate</strong> (3 g, 11.8 mmol) and NaH (945 mg, 23.6 mmol, 60% purity) in DMF (30 mL) was added MeI (3.35 g, 23.6mmol, 1.47 mL) at 0 C. The mixture was warmed to 20 C and stirred for 3 hours. TLC (petroleum ether : ethyl acetate = 5:1, Rf = 0.4) indicated that starting material was consumed completely and one new spot was formed. The reaction was quenched with water (100 mL) and extracted with MTBE (100 mL x 3). The combined organic layer was washed with water (80 mL x 2) and brine (80 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to give methyl 4-bromo-1,N-methylindole-6-carboxylate (3.34 g, crude) as a yellow solid. 1H NMR 400 MHz CDCl3 = 8.06 (s, 1H), 7.99 (s, 1H), 7.27 (d, J=1.6 Hz, 1H), 6.58 (d, J=2.8 Hz, 1H), 3.96(s, 3H), 3.87 (s, 3H). ESI-MS (m/z): 268.0 (M+H)+

Reference： [1]Patent: WO2017/120429,2017,A1 .Location in patent: Page/Page column 272

19
[ 882679-96-1 ]
1-(tert-butyl) 6-methyl 4-(3-ethylphenyl)indoline-1,6-dicarboxylate [ No CAS ]

Reference： [1]Patent: WO2017/141036,2017,A1

20
[ 882679-96-1 ]
1-(tert-butoxycarbonyl)-4-(3-ethylphenyl)indoline-6-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2017/141036,2017,A1

21
[ 882679-96-1 ]
tert-butyl 4-(3-ethylphenyl)-6-(methylcarbamoyl)indoline-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/141036,2017,A1

22
[ 882679-96-1 ]
4-(3-ethylphenyl)-N-methylindoline-6-carboxamide trifluoroacetate [ No CAS ]

Reference： [1]Patent: WO2017/141036,2017,A1

23
[ 882679-96-1 ]
[ 24424-99-5 ]
1-(tert-butyl)6-methyl 4-bromoindoline-1,6-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.0 g	With triethylamine; In tetrahydrofuran; at 20℃; for 16h;	To a solution of methyl 4-bromoindoline-6-carboxylate (2.40 g, 9.37 mmol) in THF (20 ml) were added TEA (1.14 ml, 11.3 mmol) followed by BOC-anhydride (2.46 g, 11.3 mmol) at rt. The reaction mixture was stirred at rt for 16 h. The reaction mixture was poured into water (100 ml) and extracted with EtOAc (2 x 100 ml). The combined organic phase was collected, dried over Na2SO4, filtered and concentrated under reduced pressure. The cmde material was purified by column chromatography (5-7% EtOAc in hexane) yielding 1 -(tert-butyl) 6-methyl 4-bromoindoline- 1 ,6-dicarboxylate (3.00 g, 8.42 mmol). LCMS: Method C, 2.846 mi MS: ES+ 373.39, 375.39 [M+18j.

Reference： [1]Patent: WO2017/141036,2017,A1 .Location in patent: Page/Page column 90

24
[ 882679-96-1 ]
(S)-4-bromo-3-hydrazono-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid [3-(2-hydroxymethyl-pyrrolidin-1-yl)-propyl]-amide [ No CAS ]

Reference： [1]Patent: WO2006/101937,2006,A1

25
[ 882679-96-1 ]
(S)-4-bromo-3-[(2-2,3-dihydro-benzofuran-5-yl-acetyl)-hydrazono]-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid [3-(2-hydroxymethyl-pyrrolidin-1-yl)-propyl]-amide [ No CAS ]

Reference： [1]Patent: WO2006/101937,2006,A1

26
[ 882679-96-1 ]
[ 910806-45-0 ]

Reference： [1]Patent: WO2006/101937,2006,A1

27
[ 882679-96-1 ]
[ 910806-48-3 ]

Reference： [1]Patent: WO2006/101937,2006,A1

28
[ 882679-96-1 ]
[ 910806-46-1 ]

Reference： [1]Patent: WO2006/101937,2006,A1

29
[ 882679-96-1 ]
2-chloro-4-(6-cyano-1-methyl-1H-indol-4-yl)pyrimidine [ No CAS ]