Propargyl alcohol → HCID 68380182, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-{2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamide (Example 33) (195 mg, 0.372 mmol), propargyl alcohol (0.033 mL, 0.558 mmol), copper(I) iodide (7.09 mg, 0.037 mmol), bis(triphenylphosphine)palladium(II) chloride (10.45 mg, 0.015 mmol) and triethylamine (0.156 mL, 1.117 mmol) in THF (1.7 mL) was stirred under an atmosphere of nitrogen at 70° C. for 3 h. The mixture was allowed to cool to RT, with stirring, over the weekend. The mixture was then partitioned between a saturated aqueous solution of NaHCO3 (25 mL) and ethyl acetate (50 mL). The aqueous phase was separated and extracted with additional ethyl acetate (25 mL). The organic extracts were combined, washed with brine (25 mL), dried with anhydrous MgSO4, filtered and evaporated to dryness. The residue was purified on silica, eluting with a gradient of 0-100% cyclohexane in ethyl acetate. Further purification on silica, eluting with 0-50% cyclohexane in ethyl acetate, afforded the title compound (14 mg) LCMS (A) m/z: 499 [M+1]+, Rt 1.24 min (acidic).

Provenance & Evidence