Water → 4-{[3-(4-Hydroxy-phenyl)-6-methyl-imidazo[1,2-a]pyrazin-8-ylamino]-methyl}-benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-[(3-bromo-6-methyl-imidazo[1,2-a]pyrazin-8-ylamino)-methyl]-benzenesulfonamide (0.1 g, 0.252 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (0.061 g, 0.277 mmol), K2CO3 1.5M in water (0.34 mL, 0.504 mmol), Pd(OAc)2 (3.0 mg, 0.013 mmol), and (oxidi-2,1-phenylene)bis(diphenylphosphine) (14 mg, 0.026 mmol) in DMF 1 mL was stirred at 88° C. overnight. Then the reaction mixture is filtered through cotton, diluted with AcOEt, washed with water, the organic layer dried with MgSO4 (anhydrous), filtered and evaporated. The crude mixture is purified by prep. HPLC under acid conditions using a gradient of 0.1% formic acid in H2O/0.1% formic acid in acetonitrile (95/5:5 min, 9/1:13 min, 0/1:4 min) to give 4-{[3-(4-hydroxy-phenyl)-6-methyl-imidazo[1,2-a]pyrazin-8-ylamino]-methyl}-benzenesulfonamide as a brown oil (30.2 mg) LC-MS m/z 410 [M+H]+.

Provenance & Evidence