1,2-Dimethoxyethane → 3-[8-(4-p-Tolyl-imidazol-1-yl)-imidazo[1,2-a]pyrazin-6-yl]-phenylamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-8-(4-p-tolyl-imidazol-1-yl)-imidazo[1,2-a]pyrazine (4) (870 mg), 3-aminophenylboronic acid hydrochloride (511 mg), tetrakis(triphenylphosphine) palladium (Pd(PPh3)4) (142 mg), 1 M aqueous sodium carbonate (Na2CO3) (7.4ml), and 1,2-dimethoxyethane (DME) (35 ml) is heated at 90 ° C. for 16 hours. The mixture is cooled to rt, treated with water (50 ml) and extracted with ethyl acetate (3×80 ml). The extracts are washed with water (1×50 ml) and brine (1×50 ml), dried over MgSO4, and evaporated in vacuo to give a semi-solid which is triturated with diethyl ether/methanol (10:1) to give 3-[8-(4-p-Tolyl-imidazol-1-yl)-imidazo[1,2-a]pyrazin-6-yl]-phenylamine (5) (600 mg) as a cream-colored solid.

Provenance & Evidence