Cesium carbonate → 1-(2-(Difluoromethyl)pyridin-4-yl)-4-fluoro-1-(2-(pyrimidin-5-yl)pyridin-4-yl)-1H-isoindol-3-amine

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	(Pyrimidin-5-yl)boronic acid	HCID 2795193	—
Reactant	1-(2-Bromopyridin-4-yl)-1-(2-(difluoromethyl)pyridin-4-yl)-4-fluoro-1H-isoindol-3-amine	HCID 58579500	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethoxyethane ethanol water	HCID 86587095	—
Product	1-(2-(Difluoromethyl)pyridin-4-yl)-4-fluoro-1-(2-(pyrimidin-5-yl)pyridin-4-yl)-1H-isoindol-3-amine	HCID 46202741	39.6%

Reaction Conditions

Temperature	150 °C

Reaction Steps

1-(2-Bromopyridin-4-yl)-1-(2-(difluoromethyl)pyridin-4-yl)-4-fluoro-1H-isoindol-3-amine (64 mg, 0.15 mmol), 5-pyrimidinylboronic acid (23.80 mg, 0.19 mmol), [1,1′-bis (diphenylphosphino)ferrocene]palladium(II) chloride (6.03 mg, 7.39 μmol), cesium carbonate (0.035 mL, 0.44 mmol) and DME:EtOH:water (6:3:1) (3.00 mL) were put in a microwave vial and heated at 150° C. in a microwave reactor for 20 min. The reaction mixture was filtered through a syringe filter and purified by prep-HPLC. The desired fractions were pooled and freeze dried over night to give the title compound (25.7 mg, 39%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08030500B2
Source dataset	uspto-grants-2011_10
ORD ID	ord-fc951f805751437a86c026d3357e0bac
Source note	uspto-grants-2011_10