4,4,5,5-Tetramethyl[1,3,2]dioxaborolane → HCID 68109649, compound

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Reaction Steps

To a suspension of 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.05 mL, 0.33 mmol) and Rh(CO)(PPh3)2Cl (2 mg, 2.7 mmol) in dichloromethane (4 mL) at ambient temperature was added tert-butyl 8-(phenylsulfonyl)-6-vinyl-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (120 mg, 0.27 mmol). The reaction mixture was stirred for 4 h then diluted with water and extracted with dichloromethane. The organic extract was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 7:3 hexanes/ethyl acetate) to give tert-butyl 8-(phenylsulfonyl)-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (85 mg, 55%) as a white solid: 1H NMR (CDCl3, 400 MHz) δ 8.01-7.92 (m, 3H), 7.72 (br s, 1H), 7.58-7.46 (m, 3H), 4.56 (s, 2H), 3.97 (q, J=6.4 Hz, 2H), 3.83 (br s, 2H), 3.16 (t, J=6.4 Hz, 2H), 2.86 (br s, 2H), 1.51 (s, 9H), 1.39-1.19 (m, 12H).

Provenance & Evidence