Cesium carbonate → HCID 178439565, compound

Participants

Reaction Steps

A mixture of N-{1-[5-(1-methylethenyl)-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-4-piperidinyl}benzamide D8 (100 mg) and cesium carbonate (195 mg, 0.598 mmol) in THF (1.4 mL) and MeOH (0.7 mL) was stirred at room temperature for 4 hours. LCMS showed complete loss of starting material, but a few products were present. The mixture was partitioned between EtOAc (15 mL) and water (15 mL) and then the organic layer was washed with water (15 mL) and brine (15 mL) before it was dried (MgSO4), filtered and the solvent removed in vacuo. The crude product was purified by MDAP and the one clean fraction was concentrated in vacuo to give E19 (12 mg) as a white solid, 1H NMR (d6-DMSO) δ 11.88 (1H, s), 8.32 (1H, d), 8.27 (1H, s), 7.85 (2H, d), 7.51 (1H, t), 7.44 (2H, t), 7.31 (1H, s), 5.10 (2H, s), 4.10 (2H, d), 4.02 (1H, m), 2.97 (2H, t), 2.13 (3H, s), 1.83 (2H, d), 1.67 (2H, ddd), MS(ES+) 362 [M+H]+.

Provenance & Evidence