Nitrogen → 5-[5-Amino-2-(2,4-difluorophenoxyl)phenyl]-7-methylimidazo[1,5-a]pyrazin-8-one

Participants

Role	Name	HCID	Charge
Reactant	Nitrogen	HCID 947	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	4-(2,4-Difluorophenoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline	HCID 89657613	—
Reactant	5-Bromo-7-methylimidazo[1,5-a]pyrazin-8(7h)-one	HCID 118022599	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	5-[5-Amino-2-(2,4-difluorophenoxyl)phenyl]-7-methylimidazo[1,5-a]pyrazin-8-one	HCID 118022157	60%

Reaction Steps

A solution of 5-bromo-7-methylimidazo[1,5-a]pyrazin-8-one (114.0 mg, 0.5 mmol), the title compound of Example 57, step 1 (208.0 mg, 0.6 mmol), Pd(dppf)2Cl2 (37.0 mg, 0.05 mmol), NaHCO3 (126.0 mg, 1.5 mmol) in dioxane (10 mL) and H2O (1 mL) was stirred in microwave at 110° C. with N2 atmosphere for 3 hours. The solvent was evaporated to give the crude product, which was purified by column chromatography (PE:EA=3/1) to give the title compound (110 mg, 60%) as a yellow solid. 1H NMR (CDCl3 400 MHz) δ 7.94 (s, 1H), 7.82 (s, 1H), 6.93-6.82 (m, 2H), 6.79-6.74 (m, 4H), 6.41 (s, 1H), 3.50 (s, 3H). LCMS (M+H)+ 369.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09115114B2
Source dataset	uspto-grants-2015_08
ORD ID	ord-4a65bdb7cb5e4ec2ae96bc0d5e763f03
Source note	uspto-grants-2015_08