[ CAS No. 126811-29-8 ] {[proInfo.proName]}

Name: 126811-29-8|7-Bromo-4-chloro-1H-indole|95%
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Quality Control of [ 126811-29-8 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 126811-29-8 ]

CAS No. :	126811-29-8	MDL No. :	MFCD09749918
Formula :	C₈H₅BrClN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZFBAFEMIPJPWPF-UHFFFAOYSA-N
M.W :	230.49	Pubchem ID :	18752873
Synonyms :

Calculated chemistry of [ 126811-29-8 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	1.0
Molar Refractivity :	51.01
TPSA :	15.79 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.31 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.14
Log Po/w (XLOGP3) :	3.37
Log Po/w (WLOGP) :	3.58
Log Po/w (MLOGP) :	2.87
Log Po/w (SILICOS-IT) :	3.84
Consensus Log Po/w :	3.16

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.0
Solubility :	0.0232 mg/ml ; 0.000101 mol/l
Class :	Soluble
Log S (Ali) :	-3.38
Solubility :	0.0961 mg/ml ; 0.000417 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.76
Solubility :	0.00401 mg/ml ; 0.0000174 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.52

Safety of [ 126811-29-8 ]

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 [ 126811-29-8 ]

* 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.

Upstream synthesis route of [ 126811-29-8 ]
Downstream synthetic route of [ 126811-29-8 ]

[ 126811-29-8 ] Synthesis Path-Upstream 1~3

1
[ 41513-04-6 ]
[ 1826-67-1 ]
[ 126811-29-8 ]

Yield	Reaction Conditions	Operation in experiment
49%	at -45 - -40℃; for 0.5 h;	Example S65; Preparation of 4-chloro-1H-indole-7-carboxylic acid; 1.19 g (5 mmol) of 2-bromo-5-chloro-nitrobenzene were dissolved in 50 ml THF. At a temperature of -45° C. 15 ml of a 1M vinyl magnesium bromide solution in THF were added under nitrogen in such a way that the temperature did not exceed -40° C. After complete addition the dark solution was stirred for 30 min at -40° C. The reaction mixture was quenched with 10 ml aqueous saturated ammonium chloride solution and extracted twice with diethyl ether. The combined organic layers were washed once with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was purified by column chromatography (100 g silica gel; heptane/EtOAc 19:1) to yield 562 mg (49percent) of 7-bromo-4-chloro-1H-indole as an orange oil. MS (EI) 229.0 (80), 231.0 (100), 233.0 (30) (M)⁺.
47%	at -45℃; for 1 h;	To a stirred solution of l-bromo-4chloro-2-nitrobenzene (1.3g, 5.49mmol) in THF(28ml) was added vinylmagnesium bromide (1M in THF, 16.5ml, 123mmol) at -45°C and the reaction mixture was stirred at the same temperature for lhour. Then the reaction mixture was quenched with saturated NH4CI (20ml). The volatile components were evaporated under reduced pressure and H₂0 (30ml) was added to the resulting residue. The crude was extracted with DCM (2x 15ml) and the organic layer was washed with brine (50ml) dried over Na₂S0₄ and concentrated in vacuo. The residue was purified by flash - - chromatography using AcOEt/Heptane (1/19) to give the title compound as a yellow oil (0.6g, 47percent) NMR (400MHZ, CDC1₃): 8.35 (s, 1H, br), 7.22 (t, 1H, J= 2.8Hz), 7.17 (d, 1H, J= 8Hz) 6.94 (d, J=8Hz, 1H), 6.66 (t, 1H, J= 2.8Hz) 1³C NMR (100 MHz, CDCI3): 135.0, 127.5, 125.6, 125.2, 124.7, 120.7, 102.8
44%	at -40℃; for 1 h;	Preparation 44 7-Bromo-4-chloro-1H-indole To a solution of 1-bromo-4-chloro-2-nitrobenzene (932 mg, 3.95 mmol) in tetrahydrofuran (10 mL), vinylmagnesium bromide (0.7 M in tetrahydrofuran) (12 mmol) in tetrahydrofuran (15 mL) was added drop wise at -40° C. After 1 h the reaction mixture was poured into saturated NH₄Cl. The resulting organic layer was concentrated. The resulting residue was purified using a Teledyne ISCO chromatography system with a gradient eluent system of 2percent ethyl acetate in hexane to yield the title compound (400 mg, 44percent): ¹H NMR (300 MHz, CDCl₃) δ 6.73 (t, J=2.8 Hz, 1H), 7.02 (d, J=8.1 Hz, 1H), 7.19-7.39 (m, 2H), 8.43 (s, 1H).

32%

at -40℃; for 1 h; Inert atmosphere

Under a nitrogen gas, 1-bromo-4-chloro- 2-nitrobenzene (25g, 0.107mol) was dissolved in THF (250mL), added dropwise vinylmagnesium bromide (1M in THF, 321mL , 0.321mol) in -40 degree celcius , and then slowly was stirred at -40 degree celcius for 1 hour. Since, NH₄After completion of the reaction with Cl aqueous solution was raised to room temperature.Then, ethyl acetate and the organic layer was extracted with, MgSO₄to remove water from the organic layer to the next, filtered and concentrated and purified by column chromatography with 7-bromo-4-chloro-1H-indole (7.89g,Yield: 32percent) It was obtained.

Reference： [1] Patent: US2006/30613, 2006, A1, . Location in patent: Page/Page column 35
[2] Patent: WO2016/16370, 2016, A1, . Location in patent: Page/Page column 39; 40
[3] Patent: US2014/274695, 2014, A1, . Location in patent: Paragraph 0292; 0293
[4] Patent: KR101601357, 2016, B1, . Location in patent: Paragraph 0328-0330
[5] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 11, p. 1223 - 1226
[6] Patent: WO2009/86139, 2009, A1, . Location in patent: Page/Page column 268
[7] Patent: WO2012/21591, 2012, A1, . Location in patent: Page/Page column 148

2
[ 41513-04-6 ]
[ 126811-29-8 ]

Reference： [1] Patent: US5721246, 1998, A,

3
[ 124-38-9 ]
[ 126811-29-8 ]
[ 875305-77-4 ]

Yield	Reaction Conditions	Operation in experiment
67%	Stage #1: With n-butyllithium In tetrahydrofuran at -78 - 5℃; for 0.5 h; Stage #2: at -78 - 20℃; for 0.25 h;	560 mg (2.43 mmol) of 7-bromo-4-chloro-1H-indole were dissolved in 15 ml THF. The reaction mixture was cooled to -78° C. and 4.55 ml of a 1.6 M butyl lithium solution in hexane were added under nitrogen in such a way, that the temperature did not exceed a maximum of -70° C. The yellow solution was stirred at 0 to 5° C. after complete addition for 30 min. The reaction mixture was cooled to -78° C. and dry ice was added. The reaction mixture was warmed to rt, stirred for 15 min and poured onto 100 ml water. The aqueous layer was washed twice with diethyl ether, acidified with 1N aqueous HCl solution and extracted twice with diethyl ether. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated. The crude residue was stirred with hexane for 15 min, filtered and dried to yield 319 mg (67percent) of 4-chloro-1H-indole-7-carboxylic acid as an off-white solid. MS (ISP) 194.1 (M-H)^-.

Reference： [1] Patent: US2006/30613, 2006, A1, . Location in patent: Page/Page column 35

[ 126811-29-8 ] Synthesis Path-Downstream 1~32

1
[ 41513-04-6 ]
[ 1826-67-1 ]
[ 126811-29-8 ]

Yield	Reaction Conditions	Operation in experiment
49%	In tetrahydrofuran; at -45 - -40℃; for 0.5h;	Example S65; Preparation of 4-chloro-1H-indole-7-carboxylic acid; 1.19 g (5 mmol) of 2-bromo-5-chloro-nitrobenzene were dissolved in 50 ml THF. At a temperature of -45 C. 15 ml of a 1M vinyl magnesium bromide solution in THF were added under nitrogen in such a way that the temperature did not exceed -40 C. After complete addition the dark solution was stirred for 30 min at -40 C. The reaction mixture was quenched with 10 ml aqueous saturated ammonium chloride solution and extracted twice with diethyl ether. The combined organic layers were washed once with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was purified by column chromatography (100 g silica gel; heptane/EtOAc 19:1) to yield 562 mg (49%) of 7-bromo-4-chloro-1H-indole as an orange oil. MS (EI) 229.0 (80), 231.0 (100), 233.0 (30) (M)+.
47%	In tetrahydrofuran; at -45℃; for 1h;	To a stirred solution of l-bromo-4chloro-2-nitrobenzene (1.3g, 5.49mmol) in THF(28ml) was added vinylmagnesium bromide (1M in THF, 16.5ml, 123mmol) at -45C and the reaction mixture was stirred at the same temperature for lhour. Then the reaction mixture was quenched with saturated NH4CI (20ml). The volatile components were evaporated under reduced pressure and H20 (30ml) was added to the resulting residue. The crude was extracted with DCM (2x 15ml) and the organic layer was washed with brine (50ml) dried over Na2S04 and concentrated in vacuo. The residue was purified by flash - - chromatography using AcOEt/Heptane (1/19) to give the title compound as a yellow oil (0.6g, 47%) NMR (400MHZ, CDC13): 8.35 (s, 1H, br), 7.22 (t, 1H, J= 2.8Hz), 7.17 (d, 1H, J= 8Hz) 6.94 (d, J=8Hz, 1H), 6.66 (t, 1H, J= 2.8Hz) 13C NMR (100 MHz, CDCI3): 135.0, 127.5, 125.6, 125.2, 124.7, 120.7, 102.8
44%	In tetrahydrofuran; at -40℃; for 1h;	Preparation 44 7-Bromo-4-chloro-1H-indole To a solution of 1-bromo-4-chloro-2-nitrobenzene (932 mg, 3.95 mmol) in tetrahydrofuran (10 mL), vinylmagnesium bromide (0.7 M in tetrahydrofuran) (12 mmol) in tetrahydrofuran (15 mL) was added drop wise at -40 C. After 1 h the reaction mixture was poured into saturated NH4Cl. The resulting organic layer was concentrated. The resulting residue was purified using a Teledyne ISCO chromatography system with a gradient eluent system of 2% ethyl acetate in hexane to yield the title compound (400 mg, 44%): 1H NMR (300 MHz, CDCl3) delta 6.73 (t, J=2.8 Hz, 1H), 7.02 (d, J=8.1 Hz, 1H), 7.19-7.39 (m, 2H), 8.43 (s, 1H).

32%	In tetrahydrofuran; at -40℃; for 1h;Inert atmosphere;	Under a nitrogen gas, 1-bromo-4-chloro- 2-nitrobenzene (25g, 0.107mol) was dissolved in THF (250mL), added dropwise vinylmagnesium bromide (1M in THF, 321mL , 0.321mol) in -40 degree celcius , and then slowly was stirred at -40 degree celcius for 1 hour. Since, NH4After completion of the reaction with Cl aqueous solution was raised to room temperature.Then, ethyl acetate and the organic layer was extracted with, MgSO4to remove water from the organic layer to the next, filtered and concentrated and purified by column chromatography with 7-bromo-4-chloro-1H-indole (7.89g,Yield: 32%) It was obtained.
		7-Bromo-4-chloro-lH-indole was prepared from l-bromo-4-chloro-2-nitrobenzene and vinylmagnesium bromide using Bartoli indole synthesis condition (Tetrahedron Letters, 1989, Vol. 30, 2129-2132).
		Example 17, Step aTo a stirred solution of 1 -bromo-4-chloro-2-nitrobenzene (10 g, 42.3 mmol) in THF (125 mL) was added vinylmagnesium bromide (1M in THF, 127 mL, 127 mmol) at -78 C and the reaction mixture was stirred at the same temperature for 30 minutes. Then the reaction mixture was quenched with saturated NH4C1 (60 mL). The volatile components were evaporated under reduced pressure and H20 (100 mL) was added to the resulting residue. The crude was extracted with DCM (2 x 50 mL), and the organic layer was washed with brine (50 mL), dried over Na2S04 and concentrated in vacuo. The residue was purified by flash chromatography (Silica gel 230-400, 1.3 % EtO Ac/petroleum ether) to yield 17a (4.5 g) as brown oil. LC/MS (Condition 15): Rt = 2.01 min. 'H NMR (DMSO-d6, delta = 2.50 ppm, 400 MHz): delta 11.72 (br s, 1H), 7.52 (t, J = 2.8, 1H), 7.32 (d, J = 8.0, 1H), 7.05 (d, J = 8.0, 1H), 6.61-6.59 (m, 1H). LC/MS: Anal. Calcd. for [M-H]" C8H4BrClN: 227.93; found 228.0.

Reference： [1]Patent: US2006/30613,2006,A1 .Location in patent: Page/Page column 35
[2]Patent: WO2016/16370,2016,A1 .Location in patent: Page/Page column 39; 40
[3]Patent: US2014/274695,2014,A1 .Location in patent: Paragraph 0292; 0293
[4]Patent: KR101601357,2016,B1 .Location in patent: Paragraph 0328-0330
[5]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1223 - 1226
[6]Patent: WO2009/86139,2009,A1 .Location in patent: Page/Page column 268
[7]Patent: WO2012/21591,2012,A1 .Location in patent: Page/Page column 148

2
[ 126811-29-8 ]
7-azido-4-chloro-1H-indole [ No CAS ]