[ CAS No. 1186663-45-5 ] {[proInfo.proName]}

Name: 1186663-45-5|Methyl 3-Bromo-1-methylindole-6-carboxylate|95%
Brand: Ambeed
SKU: A410188
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Quality Control of [ 1186663-45-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1186663-45-5 ]

CAS No. :	1186663-45-5	MDL No. :	MFCD12828701
Formula :	C₁₁H₁₀BrNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BNUJUFJNYWGDTC-UHFFFAOYSA-N
M.W :	268.11	Pubchem ID :	53429640
Synonyms :

Calculated chemistry of [ 1186663-45-5 ]

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) :	2.75
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 :	2.57

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 :	1.71

Safety of [ 1186663-45-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1186663-45-5 ]

* 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 [ 1186663-45-5 ]

[ 1186663-45-5 ] Synthesis Path-Downstream 1~33

1
[ 860457-92-7 ]
[ 74-88-4 ]
methyl 3-bromo-1-methyl-1H-indole-6-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.978 g		Potassium carbonate (1.681 g, 12.16 mmol) was added to a solution of methyl3-bromo-1H-indole-6-carboxylate (1.0299 g, 4.05 mmol) in DMF (10 mL) at roomtemperature. The mixture was stirred at room temperature for 30 mm. The reaction mixture was cooled to 0 C and methyl iodide (0.304 mL, 4.86 mmol) was added. The reaction was stirred overnight while it warmed up to room temperature. The reaction was diluted with water and extracted with diethyl ether three times. The diethyl ether layers were combined, dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified via silica gel flash column chromatography eluting with ethyl acetate in hexane from 0 to 25% to affored thetitle compound as a white solid (0.97 8 g, 90% yield). ?H NMR (400MHz, CHLOROFORM-d)oe 8.12-8.09 (m, 1H), 7.88 (dd,J=8.4, 1.4 Hz, 1H), 7.59(dd, J=8.4, 0.6 Hz, 1H), 7.24 (s, 1H), 3.97 (s, 3H), 3.87 (s, 3H); LCMS (ESI) m/e 268.0 [(M-H), calcd 268.01; LC/MS retention time (method B): tR = 1.80 mm.

Reference： [1]Patent: WO2017/184658,2017,A1 .Location in patent: Page/Page column 20; 21
[2]Journal of Medicinal Chemistry,2019,vol. 62,p. 831 - 856

2
[ 1186663-45-5 ]
[ 2142608-42-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: lithium hydroxide; water / tetrahydrofuran; methanol / 24 h / 20 °C 2.1: 2-chloro-1-methyl-pyridinium iodide / dichloromethane / 0.17 h / 20 °C 2.2: 0.17 h / 20 °C 2.3: 1 h / 20 °C 3.1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 2 h / 100 °C

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2017/184658, 2017, A1

3
[ 1186663-45-5 ]
[ 1784172-44-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 24h;	Intermediate E: 3 -Bromo- 1-methyl- 1H-indole-6-carboxylic acid A mixture of LiOH (0.172 g, 7.20 mmol) and methyl 3-bromo-1-methyl-1H- indole-6-carboxylate (0.965 g, 3.60 mmol) in THF (4 mL), water (1.5 mL), and MeOH (1.5 mL) was stirred at room temperature for 24 hours. The volatiles were removed under vacuum and iN HC1 (6 mL) was added to the residue. The slurry was filtered and the solid was collected via vacuum filtration and washed with water. The solid was taken up in ethyl acetate and dried with Na2SO4. The ethyl acetate layerwas filtered and concentrated under reduced pressure to give the title product as awhite solid (0.837 g, 92% yield). The material was carried forward without furtherpurification. ‘H NMR (400MHz, CHLOROFORM-d) ö 8.17 (s, 1H), 7.93 (dd, J=8.3,1.3 Hz, 1H), 7.63 (d, J=8.5 Hz, 1H), 7.28 (s, 1H), 3.89 (s, 3H); LCMS (ESI) m/e252.0 [(M-H), calcd C10H7Br1N1O2, 251.91; LC/MS retention time (method B): tR =1.17 mm.
	With lithium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 36h; Inert atmosphere;

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2017/184658, 2017, A1 Location in patent: Page/Page column 21; 22
[2]Luo, Guanglin; Chen, Ling; Easton, Amy; Newton, Amy; Bourin, Clotilde; Shields, Eric; Mosure, Kathy; Soars, Matthew G.; Knox, Ronald J.; Matchett, Michele; Pieschl, Rick L.; Post-Munson, Debra J.; Wang, Shuya; Herrington, James; Graef, John; Newberry, Kimberly; Sivarao, Digavalli V.; Senapati, Arun; Bristow, Linda J.; Meanwell, Nicholas A.; Thompson, Lorin A.; Dzierba, Carolyn [Journal of Medicinal Chemistry, 2019, vol. 62, # 2, p. 831 - 856]

4
[ 1186663-45-5 ]
[ 2142608-33-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: lithium hydroxide; water / tetrahydrofuran; methanol / 24 h / 20 °C 2.1: 2-chloro-1-methyl-pyridinium iodide / dichloromethane / 0.17 h / 20 °C 2.2: 0.17 h / 20 °C 2.3: 1 h / 20 °C
	Multi-step reaction with 2 steps 1: lithium hydroxide / water; methanol; tetrahydrofuran / 36 h / 20 °C / Inert atmosphere 2: 2-chloro-1-methyl-pyridinium iodide; dmap; triethylamine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2017/184658, 2017, A1
[2]Luo, Guanglin; Chen, Ling; Easton, Amy; Newton, Amy; Bourin, Clotilde; Shields, Eric; Mosure, Kathy; Soars, Matthew G.; Knox, Ronald J.; Matchett, Michele; Pieschl, Rick L.; Post-Munson, Debra J.; Wang, Shuya; Herrington, James; Graef, John; Newberry, Kimberly; Sivarao, Digavalli V.; Senapati, Arun; Bristow, Linda J.; Meanwell, Nicholas A.; Thompson, Lorin A.; Dzierba, Carolyn [Journal of Medicinal Chemistry, 2019, vol. 62, # 2, p. 831 - 856]

5
[ 1186663-45-5 ]
[ 2142608-34-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: lithium hydroxide; water / tetrahydrofuran; methanol / 24 h / 20 °C 2.1: 2-chloro-1-methyl-pyridinium iodide / dichloromethane / 0.17 h / 20 °C 2.2: 0.17 h / 20 °C 2.3: 1 h / 20 °C 3.1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 2 h / 100 °C
	Multi-step reaction with 3 steps 1: lithium hydroxide / water; methanol; tetrahydrofuran / 36 h / 20 °C / Inert atmosphere 2: 2-chloro-1-methyl-pyridinium iodide; dmap; triethylamine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere

6
[ 50820-65-0 ]
[ 1186663-45-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 2 h / -60 - 20 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C 2.2: 0 °C
	Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 2 h / -60 - 20 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere

7
[ 1810773-33-1 ]
[ 1186663-45-5 ]
[ 2131191-83-6 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; potassium carbonate; trans-N,N'-dimethylcyclohexane-1,2-diamine In toluene at 110℃; Inert atmosphere;

Reference： [1]Shaw, Subrata; Bian, Zhiguo; Zhao, Bin; Tarr, James C.; Veerasamy, Nagarathanam; Jeon, Kyu Ok; Belmar, Johannes; Arnold, Allison L.; Fogarty, Stuart A.; Perry, Evan; Sensintaffar, John L.; Camper, Demarco V.; Rossanese, Olivia W.; Lee, Taekyu; Olejniczak, Edward T.; Fesik, Stephen W. [Journal of Medicinal Chemistry, 2018, vol. 61, # 6, p. 2410 - 2421]

8
[ 1810773-33-1 ]
[ 1186663-45-5 ]
[ 2131184-49-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trans-N,N'-dimethylcyclohexane-1,2-diamine; potassium carbonate; copper(l) iodide / toluene / 110 °C / Inert atmosphere 2: lithium hydroxide / water / 40 °C

9
[ 1186663-45-5 ]
[ 2142608-46-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: lithium hydroxide / water; methanol; tetrahydrofuran / 36 h / 20 °C / Inert atmosphere 2: 2-chloro-1-methyl-pyridinium iodide; dmap; triethylamine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere

Reference： [1]Luo, Guanglin; Chen, Ling; Easton, Amy; Newton, Amy; Bourin, Clotilde; Shields, Eric; Mosure, Kathy; Soars, Matthew G.; Knox, Ronald J.; Matchett, Michele; Pieschl, Rick L.; Post-Munson, Debra J.; Wang, Shuya; Herrington, James; Graef, John; Newberry, Kimberly; Sivarao, Digavalli V.; Senapati, Arun; Bristow, Linda J.; Meanwell, Nicholas A.; Thompson, Lorin A.; Dzierba, Carolyn [Journal of Medicinal Chemistry, 2019, vol. 62, # 2, p. 831 - 856]

10
[ 1186663-45-5 ]
[ 2142608-47-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: lithium hydroxide / water; methanol; tetrahydrofuran / 36 h / 20 °C / Inert atmosphere 2: 2-chloro-1-methyl-pyridinium iodide; dmap; triethylamine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere

11
[ 1186663-45-5 ]
[ 2142608-39-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: lithium hydroxide / water; methanol; tetrahydrofuran / 36 h / 20 °C / Inert atmosphere 2: 2-chloro-1-methyl-pyridinium iodide; dmap; triethylamine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere

12
[ 1186663-45-5 ]
[ 2142608-40-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: lithium hydroxide / water; methanol; tetrahydrofuran / 36 h / 20 °C / Inert atmosphere 2: 2-chloro-1-methyl-pyridinium iodide; dmap; triethylamine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere

13
[ 1186663-45-5 ]
[ 2142608-45-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: lithium hydroxide / water; methanol; tetrahydrofuran / 36 h / 20 °C / Inert atmosphere 2: 2-chloro-1-methyl-pyridinium iodide; dmap; triethylamine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere

14
[ 1186663-45-5 ]
[ 2412364-87-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: lithium hydroxide / water; methanol; tetrahydrofuran / 36 h / 20 °C / Inert atmosphere 2: 2-chloro-1-methyl-pyridinium iodide; dmap; triethylamine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane / 4 h / 80 °C / Inert atmosphere

15
[ 1186663-45-5 ]
[ 2412364-88-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: lithium hydroxide / water; methanol; tetrahydrofuran / 36 h / 20 °C / Inert atmosphere 2: 2-chloro-1-methyl-pyridinium iodide; dmap; triethylamine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane / 4 h / 80 °C / Inert atmosphere

16
[ 1186663-45-5 ]
[ 2142608-50-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: lithium hydroxide / water; methanol; tetrahydrofuran / 36 h / 20 °C / Inert atmosphere 2: 2-chloro-1-methyl-pyridinium iodide; dmap; triethylamine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere

17
[ 1186663-45-5 ]
[ 2142608-49-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: lithium hydroxide / water; methanol; tetrahydrofuran / 36 h / 20 °C / Inert atmosphere 2: 2-chloro-1-methyl-pyridinium iodide; dmap; triethylamine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere

18
[ 1186663-45-5 ]
[ 2142608-52-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: lithium hydroxide / water; methanol; tetrahydrofuran / 36 h / 20 °C / Inert atmosphere 2: 2-chloro-1-methyl-pyridinium iodide; dmap; triethylamine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere

19
[ 1186663-45-5 ]
[ 2142608-48-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: lithium hydroxide / water; methanol; tetrahydrofuran / 36 h / 20 °C / Inert atmosphere 2: 2-chloro-1-methyl-pyridinium iodide; dmap; triethylamine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere

20
[ 1186663-45-5 ]
[ 2142608-38-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: lithium hydroxide / water; methanol; tetrahydrofuran / 36 h / 20 °C / Inert atmosphere 2: 2-chloro-1-methyl-pyridinium iodide; dmap; triethylamine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere

21
[ 1810770-12-7 ]
[ 1186663-45-5 ]
[ 2131184-67-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide; potassium phosphate / toluene / 110 °C / Sealed tube; Inert atmosphere 2: lithium hydroxide / tetrahydrofuran; methanol; water / 40 °C

Reference： [1]Lee, Taekyu; Christov, Plamen P.; Shaw, Subrata; Tarr, James C.; Zhao, Bin; Veerasamy, Nagarathanam; Jeon, Kyu Ok; Mills, Jonathan J.; Bian, Zhiguo; Sensintaffar, John L.; Arnold, Allison L.; Fogarty, Stuart A.; Perry, Evan; Ramsey, Haley E.; Cook, Rebecca S.; Hollingshead, Melinda; Davis Millin, Myrtle; Lee, Kyung-Min; Koss, Brian; Budhraja, Amit; Opferman, Joseph T.; Kim, Kwangho; Arteaga, Carlos L.; Moore, William J.; Olejniczak, Edward T.; Savona, Michael R.; Fesik, Stephen W. [Journal of Medicinal Chemistry, 2019, vol. 62, # 8, p. 3971 - 3988]

22
[ 1810770-12-7 ]
[ 1186663-45-5 ]
[ 2131192-01-1 ]

Yield	Reaction Conditions	Operation in experiment
	With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; potassium phosphate; copper(l) iodide In toluene at 110℃; Sealed tube; Inert atmosphere;

23
[ 1186663-45-5 ]
[ 2564831-08-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / toluene / 16 h / 100 °C 2.1: trifluoroacetic acid / dichloromethane / 2 h / 25 °C 3.1: dichloromethane / 0.17 h / 25 °C 3.2: 16 h / 25 °C 4.1: sodium hydroxide; water / methanol; tetrahydrofuran / 2 h / 50 °C 5.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 16 h / 25 °C