Cesium carbonate → HCID 59369872, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-({(1R,2S,5S)-3-[(5-bromo-2-methyl-1,3-thiazol-4-yl)carbonyl]-3-azabicyclo[3.1.0]hex-2-yl}methyl)-1,3-benzoxazol-2-amine (0.010 g, 0.023 mmol) and 2-tolylboronic acid (0.012 g, 0.092 mmol) in DMF (0.25 mL) was added 1M aqueous cesium carbonate (0.092 mL, 0.092 mmol) and PdCl2(dppf) (0.0016 g, 0.0023 mmol) and heated in a microwave to 130° C. for 10 minutes. The system was cooled to room temperature, extracted with EtOAc, washed with water, dried over sodium sulfate and concentrated. The crude reaction mixture was then purified using reverse phase conditions (5%→60% 0.1% TFA in water: 0.1% TFA in acetonitrile) followed by free basing with saturated sodium carbonate to afford the title compound (2-2) as a bone powder. 1H NMR (500 MHz, CDCl3) δ 7.35 (m, 1H), 7.19-7.34 (m, 5H), 7.14 (m, 1H), 7.02 (m, 1H), 4.29 (m, 1H), 3.98 (m, 1H), 3.52 (m, 2H), 3.39 (m, 1H), 2.75 (s, 3H), 2.32 (s, 3H), 1.81 (m, 1H), 1.44 (m, 1H), 0.882 (m, 1H), 0.548 (m, 1H). HRMS [M+H] C25H24N4O2S1 calc'd 445.1693, found 445.1679.

Provenance & Evidence