Cesium carbonate → HCID 24951937, compound

Participants

Reaction Steps

A mixture of 3-hydroxy-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-N-(5-methylpyrazin-2-yl)benzamide (Intermediate 18) (206 mg, 0.6 mmol), 5-bromo-N,N-dimethyl-pyridine-2-carboxamide (CAS no. 845305-86-4) (165 mg, 0.72 mmol), cesium carbonate (587 mg, 1.8 mmol) and tris(triphenylphosphine)copper bromide (CAS no. 15709-74-7) (112 mg, 0.12 mmol) in N,N-dimethylacetamide (5 mL) was stirred at 160° C. for 6 hours. The N,N-dimethylacetamide was evaporated under reduced pressure and the residue was dissolved in water (20 mL) extracted with ethyl acetate (3×20 mL). The combined organic extracts were dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica eluting with 0-5% methanol in DCM. The resulting compound was dissolved in ethyl acetate (110 mL), washed with citric acid (1N, 10 mL), water (10 mL) and brine (10 mL), dried (MgSO4) and the solvent evaporated to afford the product (67 mg, 23%). 1H NMR δ (300 MHz, CDCl3) 2.14-2.26 (m, 1H), 2.52-2.67 (m, 1H), 2.55 (s, 3H), 2.94 (s, 3H), 3.15 (s, 6H), 3.34-3.57 (m, 2H), 4.94 (t, 1H), 6.97 (s, 1H), 7.23 (s, 1H), 7.40 (d, 1H), 7.46 (s, 1H), 7.72 (s, 1H), 8.14 (s, 1H), 8.38 (s, 1H), 8.58 (s, 1H), 9.52 (s, 1H); m/z 491 (M+H+).

Provenance & Evidence