[ CAS No. 1090903-58-4 ] {[proInfo.proName]}

Name: 1090903-58-4|Methyl 5-bromo-1-methyl-1H-indole-7-carboxylate|97%
Brand: Ambeed
SKU: A1233205
Rating: 98 (22 reviews)

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Quality Control of [ 1090903-58-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1090903-58-4 ]

SDS Specification

Alternatived Products of [ 1090903-58-4 ]

Product Details of [ 1090903-58-4 ]

CAS No. :	1090903-58-4	MDL No. :	MFCD32011634
Formula :	C₁₁H₁₀BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PXWCGFMBIZJCOC-UHFFFAOYSA-N
M.W :	268.11	Pubchem ID :	59497666
Synonyms :

Calculated chemistry of [ 1090903-58-4 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.18
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	62.18
TPSA :	31.23 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) :	-6.13 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.67
Log Po/w (XLOGP3) :	2.54
Log Po/w (WLOGP) :	2.73
Log Po/w (MLOGP) :	2.36
Log Po/w (SILICOS-IT) :	2.46
Consensus Log Po/w :	2.55

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.41
Solubility :	0.103 mg/ml ; 0.000385 mol/l
Class :	Soluble
Log S (Ali) :	-2.84
Solubility :	0.385 mg/ml ; 0.00144 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.77
Solubility :	0.045 mg/ml ; 0.000168 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.76

Safety of [ 1090903-58-4 ]

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 [ 1090903-58-4 ]

* 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 [ 1090903-58-4 ]

[ 1090903-58-4 ] Synthesis Path-Downstream 1~22

1
[ 860624-89-1 ]
[ 74-88-4 ]
[ 1090903-58-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: methyl 5-bromo-1H-indole-7-carboxylate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: methyl iodide In N,N-dimethyl-formamide for 0.5h;	66 A solution of the S-bromo-indole^-carboxylic acid methyl ester (300 mg, 1.18 mmol) in DMF (15 mL) was cooled to O0C under nitrogen and treated with sodium hydride (60% in mineral oil) (56.6 gm, 1.4 mmol). After stirring for 15 minutes the iodomethane (0.08 mL, 1.3 mmol) was introduced and the cooling bath was removed (reaction became light purple). After 30 minutes the reaction was quenched with water (5ml) and then concentrated to reduce the volume of DMF. The reaction was poured into water (1.6L) and EtOAc (200ml). The layers were separated and the aqueous phase was extracted with EtOAc (3x200ml). The combined organics were washed with water (3x) and then dried (MgSO4). The solution was filtered and the filterate was concentrated. The residue was purfied by CombiFlash with 10% EtOAc in Hexane as the eluent to afford the desirable product 5-Bromo-l -methyl- l//-indole-7-carboxylic acid methyl ester (290 mg, 92%) as a white solid.
32%	Stage #1: methyl 5-bromo-1H-indole-7-carboxylate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 25℃; for 0.5h;	To a solution of methyl 5-bromoindole-7-carboxylate (4.5 g, 17.7 mmol) in DMF (100 mL) at 0 °C was added NaH (1.06 g, 26.6 mmol, 60% purity). The mixture was stirred at 0 °C for 15 minutes. Iodomethane (4 g, 28.2 mmol, 1.75 mL) was added and the mixture was stirred at 25 °C for 30 minutes. TLC (petroleum ether : ethyl acetate=10:1, Rf = 0.35) indicated that starting material was consumed completely and a major new spot with lower polarity was detected. The reaction mixture was diluted with water (100 mL) and extracted with EtOAc (100 mL x 2). The combined organic phase was concentrated in vacuum to afford methyl 5-bromo-1,N-methylindole-7-carboxylate (1.5 g, 32% yield) as a brown liquid. 1H NMR 400 MHz DMSO = 7.99 (s, 1H), 7.58 (s, 1H), 7.46 (d, J=3.2 Hz, 1H), 6.56 (d, J=3.2 Hz, 1H), 3.91(s, 3H), 3.79 (s, 3H). ESI-MS (m/z): 268.0 (M+H)+

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2008/147697, 2008, A1 Location in patent: Page/Page column 239-240
[2]Current Patent Assignee: SIHUAN PHARMACEUTICAL HOLDINGS GROUP LTD. - WO2017/120429, 2017, A1 Location in patent: Page/Page column 269

2
[ 1090903-58-4 ]
[ 1090903-59-5 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: methyl 5-bromo-1,N-methylindole-7-carboxylate With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; Stage #2: With water; sodium hydrogencarbonate In diethyl ether	66 To a solution of 5-Bromo-l -methyl- l//-indole-7-carboxylic acid methyl ester (260 mg, 0.97 mmol) in Et2θ (50 mL) was added LAH (40.5 mg, 1.1 mmol) at 0 C under nitrogen atmosphere. The solution was warmed to room temperature. Sat. NaHCO3 was added and the solution was extracted with EtOAc. The combined organic layer was dried with MgSO4 and was filtered. The filtrate was concentrated and the residue was purified by CombiFlash with 50% EtOAc in Hexane as the eluent to afford the desirable product (5-Bromo-l -methyl- l//-indol-7-yl)- methanol (200 mg, 86%) as colorless oil.

Reference： [1]Current Patent Assignee: C.H. Boehringer Sohn AG & Co. KG - WO2008/147697, 2008, A1 Location in patent: Page/Page column 239-240

3
[ 143262-10-6 ]
[ 1090903-58-4 ]