Sodium Carbonate → N-(3-(3-(1-(3-cyanobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methane sulfonamide

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	3-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)benzonitrile	HCID 71092746	—
Reactant	N-(3-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide	HCID 90030209	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water 1,2-dimethoxyethane	HCID 18180031	—
Product	N-(3-(3-(1-(3-cyanobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methane sulfonamide	HCID 90031340	41.3%

Reaction Steps

Using similar reaction conditions as described in step-ii of example-1, N-(3-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide (Intermediate 9) (200 mg, 0.35 mmol) was coupled with 3-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)benzonitrile (Intermediate 14) (119.8 mg, 0.38 mmol) in sodium carbonate (111 mg, 1.05 mmol), PdCl2(dppf) (12.8 mg, 0.017 mmol) and DME/water (2/1 ml) to afford 90 mg (30% yield) of the pure product after column purification using 50% ethyl acetate in hexane as eluent.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09353107B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-f955b314fcd34dcea77a0f758a6eca07
Source note	uspto-grants-2016_05