Sodium hydride → HCID 67436158, compound

Participants

Reaction Steps

Sodium hydride (5.2 mg, 0.13 mmol, 60% in mineral oil) was added to a solution of trimethyl sulfoxonium iodide (28.7 mg, 0.13 mmol) in DMSO (1 mL) at room temperature. After 30 min at room temperature, the mixture was added to a solution of the product from Step 3 (45 mg, 0.109 mmol) in DMSO (1 mL). The resultant mixture was stirred at room temperature for 10 min and quenched with saturated NaHCO3 (1 mL). After addition of ethyl acetate (80 mL), 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 1-(2-(4-(dimethylcarbamoyl)phenyl)-5H-chromeno[2,3-b]pyridin-5-yl)cyclopropanecarboxylate (12 mg, 26%). MS (ES+) m/z: 429 (M+H).

Provenance & Evidence