Bis(neopentyl glycolato)diboron → HCID 10177515, compound

Participants

Reaction Steps

3-Bromo-7-trifluoromethylimidazo[1,2-α]pyrimidine was coupled to 3-[5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-2-fluorophenyl]-4-fluoropyridine (prepared in an analogous manner to 2′-fluoro-5′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile in Example 1, using bis(neopentyl glycolato)diboron instead of bis(pinacolato)diboron in the final palladium coupling) using the procedure described in Example 65. 3-[4-Fluoro-3-(4-fluoropyridin-3-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine was isolated as a yellow solid in 36% yield after purification on silica gel eluting with dichloromethane on a gradient of diethyl ether (2-15%): δH (400 MHz, DMSO) 7.48-7.55 (2H, m), 7.63 (1H, dd, J 10 and 9), 7.94 (1H, ddd, J 9, 5 and 2), 7.99 (1H, dd, J 7 and 2), 8.33 (1H, s), 8.73 (1H, dd, J 8 and 5.5), 8.85 (1H, d, J 10), 9.38 (1H, d, J 7); m/z (ES+) 377 (M++H).

Provenance & Evidence