Methanesulfonyl chloride → HCID 67436917, compound

Participants

Reaction Steps

Methanesulfonyl chloride (0.072 mL, 0.925 mmol) was added to a mixture of the product from Step 2 (80 mg, 0.185 mmol), TEA (0.258 mL, 1.85 mmol) and DMAP (24.9 mg, 0.203 mmol) in DCM (2 mL) at 0° C. After 1 h at this temperature, the mixture was concentrated in vacuo. The residue was suspended in benzene (4 mL), treated with DBU (0.139 mL, 0.925 mmol) and stirred at room temperature for 1 h. Saturated NaHCO3 (5 mL) and ethyl acetate (100 mL) were added. The mixture was washed with water (2×10 mL), brine (10 mL), dried (MgSO4) and concentrated. The residue was purified by flash column chromatography (silica, 50-100% ethyl acetate in hexanes) to provide methyl 2-(2-(4-(dimethylcarbamoyl)phenyl)-5H-chromeno[2,3-b]pyridin-5-yl)acrylate (45 mg, 59%). MS (ES+) m/z: 415 (M+H); HPLC retention time: 1.73 min (Analytical HPLC Method F).

Provenance & Evidence