Potassium Carbonate → tert-butyl 6-methyl-8-phenylsulfonyl-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

Participants

Reaction Steps

A solution of the product of Example 44, step C (85 mg, 0.189 mmol), trimethylboraxine (0.026 mL, 0.189 mmol), potassium carbonate (78 mg, 0.567 mmol) and tetrakis-(triphenylphosphine)palladium (21.8 mg, 0.0189 mmol) in water/1,4-dioxane (1:10, 0.55 mL) was heated to 110° C. for 5 h and then stirred at ambient temperature for 15 h. The reaction mixture was then filtered through a celite bed and concentrated in vacuo to afford the crude product which was then purified by column chromatography (SiO2, 8:2 hexanes/ethyl acetate) to provide tert-butyl 6-methyl-8-phenylsulfonyl-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (43 mg, 53%): 1H NMR (CDCl3, 300 MHz) δ 7.98-7.94 (m, 3H), 7.63 (s, 1H), 7.54-7.46 (m, 3H), 4.56 (s, 2H), 3.83 (br s, 2H), 2.86 (br s, 2H), 2.51 (s, 3H), 1.51 (s, 9H).

Provenance & Evidence