Sodium Carbonate → HCID 10160106, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 3-bromo-7-trifluoromethylimidazo[1,2-α]pyrimidine (0.1073 g, 0.403 mmol) and 2-(2-fluoro-2′-(methanesulfonyl)biphenyl-5-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (228 mg, 0.607 mmol) in tetrahydrofuran (5 ml) and 2M aqueous sodium carbonate (containing 1 ml/l of 40 wt % tetrabutylammonium hydroxide in water) (0.605 ml, 1.21 mmol) was degassed by bubbling nitrogen through the mixture for 15 min. Tetrakis(triphenylphosphine)palladium(0) (24.6 mg, 0.0213 mmol) was then added and the mixture was heated at 65° C. under nitrogen for 6 h. After cooling, the mixture was partitioned between ethyl acetate (25 ml) and water (15 ml). The aqueous layer was extracted further with ethyl acetate (2×25 ml) and the combined organic extracts were dried over anhydrous sodium sulphate and evaporated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with isohexane on a gradient of ethyl acetate (40-50%), to afford 3-[2-fluoro-2′-(methanesulfonyl)biphenyl-5-yl]-7-trifluoromethylimidazo[1,2-α]pyrimidine as a yellow solid (139 mg, 79%): mp 211-213° C. (ethyl acetate/isohexane); δH (360 MHz, CDCl3) 2.89 (3H, s), 7.27 (1H, d, J 6.9), 7.40 (1H, td, J 1.2, 9.0), 7.46 (1H, dd, J 1.2, 7.4), 7.62-7.66 (2H, m), 7.68 (1H, td, J 1.6, 7.4), 7.74 (1H, td, J 1.6, 7.4), 8.10 (1H, s), 8.29 (1H, dd, J 1.4, 8.0), 9.22 (1H, d, J 7.0); MS (ES+) m/z 436 [M+H]+. Anal. Found: C, 55.02; H, 3.02; N, 9.23%. Required for C20H13F4N3O2S.0.1H2O: C, 54.94; H, 3.04; N, 9.61%.

Provenance & Evidence