Indole → HCID 68108773, compound

Participants

Reaction Steps

Sodium hydride (60% suspension in mineral oil, 19 mg, 0.484 mmol) was added to a solution of indole (42 mg, 0.363 mmol) in THF (1.5 mL) under N2 at room temperature, and the reaction stirred for 30 min. The product of step B (90 mg, 0.242 mmol) was then added and the reaction held for 2 h. It was quenched with H2O (10 mL), diluted with ether (10 mL) and the organic phase removed. The aqueous phase was extracted with ether (2×10 mL) and the combined organic phases dried over Na2SO2 and concentrated. Purification by combiflash (silica gel, hexane/ethyl acetate, 100:0 to 40:60) provided tert-butyl 8-(1H-indol-1-yl-sulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (28 mg, 25%) as a clear oil. 1H NMR (CDCl3, 300 MHz) δ 8.02 (d, J=9.0 Hz, 2H), 7.76 (dd, J=9.1, 2.2 Hz, 1H), 7.60 (d, J=4.0 Hz, 1H), 7.51 (d, J=8.4 Hz, 1H), 7.42 (d, J=8.7 Hz, 1H), 7.33 (t, J=1.4 Hz, 1H), 7.28 (t, J=1.4 Hz, 1H), 6.66 (d, J=3.6 Hz, 1H), 4.53 (br s, 2H), 3.80 (t, J=6.2 Hz, 2H), 2.82 (t, J=6.2 Hz, 2H), 1.52 (s, 9H).

Provenance & Evidence