[ CAS No. 1190309-69-3 ] {[proInfo.proName]}

Name: 1190309-69-3|3-Bromo-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile|97%
Brand: Ambeed
SKU: A199258
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Quality Control of [ 1190309-69-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1190309-69-3 ]

SDS Specification

Alternatived Products of [ 1190309-69-3 ]

Product Details of [ 1190309-69-3 ]

CAS No. :	1190309-69-3	MDL No. :	MFCD12962898
Formula :	C₈H₄BrN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZEGVAWKWFXUSRV-UHFFFAOYSA-N
M.W :	222.04	Pubchem ID :	53412566
Synonyms :

Calculated chemistry of [ 1190309-69-3 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	48.51
TPSA :	52.47 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) :	-6.43 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.52
Log Po/w (XLOGP3) :	1.72
Log Po/w (WLOGP) :	2.2
Log Po/w (MLOGP) :	1.09
Log Po/w (SILICOS-IT) :	2.64
Consensus Log Po/w :	1.83

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.86
Solubility :	0.31 mg/ml ; 0.0014 mol/l
Class :	Soluble
Log S (Ali) :	-2.44
Solubility :	0.81 mg/ml ; 0.00365 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.86
Solubility :	0.0309 mg/ml ; 0.000139 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.78

Safety of [ 1190309-69-3 ]

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

Application In Synthesis of [ 1190309-69-3 ]

* 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 [ 1190309-69-3 ]

[ 1190309-69-3 ] Synthesis Path-Downstream 1~8

1
[ 1190309-69-3 ]
[ 98-59-9 ]
[ 2481250-31-9 ]

Yield	Reaction Conditions	Operation in experiment
73%	With 4-dimethylaminopyridine; triethylamine In dichloromethane at 20℃; for 15h;	A Step A. 3-Bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile. To a flask containing 3-bromo-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (500 mg, 2.25 mmol), DMAP (55 mg, 0.45 mmol), triethylamine (0.94 ml, 6.8 mmol), and dichloromethane (15 mL) was added TosCI (515 mg, 2.70 mmol). The resultant mixture was stirred at room temperature for 15 h, then diluted with H2O (50 mL) and extracted with dichloromethane (50 mL x 3). The combined organic solvent extracts were dried over anhydrous Na2SO4 filtered, and concentrated to dryness under reduced pressure to yield the product, which was purified by FCC (eluent: petroleum ether: ethyl acetate = 1 :0 to 5:1 ) to yield 3-bromo-1-tosyl-1H- pyrrolo[2,3-b]pyridine-5-carbonitrile (680 mg, 73%) as a white solid. LCMS (ESI): mass calcd. for C15H10BrN3O2S, 376.22; m/z found, 378.0
73%	With 4-dimethylaminopyridine; triethylamine In dichloromethane at 20℃; for 15h;	A Step A. 3-Bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile. To a flask containing 3-bromo-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (500 mg, 2.25 mmol), DMAP (55 mg, 0.45 mmol), triethylamine (0.94 ml, 6.8 mmol), and dichloromethane (15 mL) was added TosCI (515 mg, 2.70 mmol). The resultant mixture was stirred at room temperature for 15 h, then diluted with H2O (50 mL) and extracted with dichloromethane (50 mL x 3). The combined organic solvent extracts were dried over anhydrous Na2SO4 filtered, and concentrated to dryness under reduced pressure to yield the product, which was purified by FCC (eluent: petroleum ether: ethyl acetate = 1 :0 to 5:1 ) to yield 3-bromo-1-tosyl-1H- pyrrolo[2,3-b]pyridine-5-carbonitrile (680 mg, 73%) as a white solid. LCMS (ESI): mass calcd. for C15H10BrN3O2S, 376.22; m/z found, 378.0
60%	Stage #1: 3-bromo-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Stage #2: 4-methylbenzene-1-sulfonyl chloride In tetrahydrofuran; mineral oil at 20℃;

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2022/104348, 2022, A1 Location in patent: Page/Page column 104; 180
[2]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2022/104348, 2022, A1 Location in patent: Page/Page column 104; 180
[3]Nimje, Roshan Y.; Vytla, Devaiah; Kuppusamy, Prakasam; Velayuthaperumal, Rajeswari; Jarugu, Lokesh Babu; Reddy, China Anki; Chikkananjaiah, Nanjundaswamy Kanikahalli; Rampulla, Richard A.; Cavallaro, Cullen L.; Li, Jianqing; Mathur, Arvind; Gupta, Anuradha; Roy, Amrita [Journal of Organic Chemistry, 2020, vol. 85, # 17, p. 11519 - 11530]

2
[ 1190309-69-3 ]
[ 98-59-9 ]
[ 2481250-07-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C 1.2: 20 °C 2.1: zinc; iodine / N,N-dimethyl-formamide / 0.58 h / 20 °C 2.2: 3 h / 55 °C

Reference： [1]Nimje, Roshan Y.; Vytla, Devaiah; Kuppusamy, Prakasam; Velayuthaperumal, Rajeswari; Jarugu, Lokesh Babu; Reddy, China Anki; Chikkananjaiah, Nanjundaswamy Kanikahalli; Rampulla, Richard A.; Cavallaro, Cullen L.; Li, Jianqing; Mathur, Arvind; Gupta, Anuradha; Roy, Amrita [Journal of Organic Chemistry, 2020, vol. 85, # 17, p. 11519 - 11530]

3
[ 1190309-69-3 ]
[ 1434747-57-5 ]