3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 46205883, compound

Participants

Reaction Conditions

Reaction Steps

Argon gas was bubbled through a mixture of 2-chloro-4-morpholinobenzofuro[3,2-d]pyrimidine (ASA66) (48.7 mg, 168 □mol, 1.0 eq) and 3-Hydroxyphenylboronic acid pinacol ester (MW 220) (148 mg, 672 □mol, 4.0 eq) in 1,2 dimethoxyethan and 2 M Na2CO3 (3:1) (4 mL) for 5 min. Dichloro 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloromethane complex (MW 732) (3.07 mg, 4.20 □mol, 0.025 eq) was added and the reaction mixture was heated to reflux (90° C.) for 15.5 h. The red solution was cooled and diluted with EtOAc (6.5 mL). The organic solution was washed with a mixture of H2O:Na2CO3:NH4OH (conc. 32% in water)=5:4:1 (6.5 mL), then NH4Cl (sat.) and brine (2×), dried over Na2CO3, filtered and concentrated. Purification by silica gel chromatography gave a colorless solid (49 mg, 85%).

Provenance & Evidence