Dichloromethane → 4-Fluoro-3-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamido)benzoic Acid

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	1-Methyl-1H-pyrazole-4-boronic acid	HCID 11263501	—
Reactant	3-[(7-Bromo-imidazo[1,2-a]pyridine-3-carbonyl)-amino]-4-fluoro-benzoic Acid Methyl Ester	HCID 71282888	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	4-Fluoro-3-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamido)benzoic Acid	HCID 71283092	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture comprising methyl 3-(7-bromoimidazo[1,2-a]pyridine-3-carboxamido)-4-fluorobenzoate (Intermediate 1A) (5.41 g, 13.79 mmol), 1-methyl-1H-pyrazol-4-ylboronic acid (1.911 g, 15.17 mmol), Pd(dppf)Cl2.DCM (1.127 g, 1.379 mmol) and cesium carbonate (13.48 g, 41.4 mmol) in DME (100 ml) and water (10 ml) was heated at 100° C. for 4 hrs. 3 equivalents of sodium carbonate were added and the mixture was heated to 100° C. for 6 hrs. A further 3 equivalents of sodium carbonate were added and the reaction was heated at 100° C. overnight.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08883819B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-ef6c0f870f63447f98a9040e80ba6368
Source note	uspto-grants-2014_11