Triethylamine → HCID 68380544, 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) (122 mg, 0.233 mmol), N,N-dimethyl-2-propyn-1-amine (0.037 mL, 0.349 mmol), copper(I) iodide (4.44 mg, 0.023 mmol), bis(triphenylphosphine)palladium(II) chloride (6.54 mg, 9.32 μmol) and triethylamine (0.097 mL, 0.699 mmol) in THF (1.0 mL) was stirred under an atmosphere of nitrogen at 70° C. for 3 h. The mixture was allowed to cool to RT and was then partitioned between saturated aqueous NaHCO3 (25 mL) and ethyl acetate (75 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 0-10% MeOH in DCM, and then further purified on silica, eluting with a gradient of 0-10% 2M NH3 in MeOH in DCM to afford the title compound (4.9 mg). 1H NMR (MeOD, 400 MHz) δ ppm: 2.42 (6H, s), 2.55 (3H, s), 3.80 (5H, s), 6.89 (2H, m), 7.01 (1H, d, J=7.7 Hz), 7.26 (1H, s), 7.32-7.48 (3H, m), 7.49-7.60 (2H, m).

Provenance & Evidence