Sodium Bicarbonate → 1,1-dimethylethyl 4-[4-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-3,6-dihydro-1(2H)-pyridinecarboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of Example 135B (260.0 mg, 0.561 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (191 mg, 0.618 mmol), Pd(Ph3P)4 (32.4 mg, 0.028 mmol), and saturated sodium bicarbonate solution (2 mL, 0.561 mmol) in N,N-dimethylformamide (8 mL) was purged with nitrogen and heated at 80° C. for 4 hours. The mixture was partitioned between ethyl acetate and brine. The organic layer was washed with brine, dried over MgSO4, and filtered. The filtrate was concentrated and the residue was separated by flash chromatography on silica gel (Teledyne CombiFlash Rf, 40% to 100% ethyl acetate in hexane) to provide the title compound. MS (ESI+) m/z 306 (M+1).

Provenance & Evidence