2-(Tributylstannyl)pyridine → HCID 10269749, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(3-bromo-4-fluorophenyl)-7-trifluoromethylimidazo[1,2-α]pyrimidine (0.190 g, 0.528 mmol) in N,N-dimethylformamide (5 ml) was added 2-tri-n-butylstannylpyridine (0.265 g) followed by dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.187 g). The mixture was heated at 100° C. for 9 h. The solvent was evaporated at reduced pressure and the residue chromatographed on silica gel eluting with 4% methanol in dichloromethane. The residue was then loaded onto a cartridge of strong cation-exchange resin. Elution with methanol gave non-basic impurities. Further elution with 2M ammonia in methanol gave crude product. Further purification by preparative thin-layer chromatography on silica gel using 4% methanol in dichloromethane as eluant and crystallisation of the residue from toluene/isohexane afforded 3-[4-fluoro-3-(pyridin-2-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine as yellow needles: δH (400 MHz, DMSO) 7.46 (1H, m), 7.53 (1H, d, J 7), 7.61 (1H, dd, J 11 and 9), 7.86-7.91 (2H, m), 7.95-7.99 (1H, m), 8.24 (1H, dd, J 7 and 2), 8.30 (1H, s), 8.74-8.76 (1H, m), 9.27 (1H, d, J 7); m/z (ES+) 359 (M++H).

Provenance & Evidence