Borane;tetrahydrofuran → HCID 86640693, compound

Participants

Reaction Steps

A 500 mL reaction flask containing 2-(6-chloropyridin-3-yl)-N-p-tolylacetamide (12 g, 46 mmol; Example 117A) in tetrahydrofuran (200 mL) was treated with 1 M borane-tetrahydrofuran (100 mL, 100 mmol; Aldrich) and then heated to reflux with stirring for 16 hours. After cooling the reaction mixture to room temperature, it was quenched with ethanol, concentrated and purified by flash chromatography (silica gel, hexanes/ethyl acetate, 2:1) to afford the title compound: 1H NMR (300 MHz, methanol-d4) δ ppm 2.19 (s, 3H), 2.89 (t, J=7 Hz, 2H), 3.35 (t, J=7 Hz, 2H), 6.56 (d, J=8 Hz, 2H), 6.93 (d, J=8 Hz, 2H), 7.37 (d, J=8 Hz, 1H), 7.70 (dd, J=8, 2 Hz, 1H), 8.21 (d, J=2 Hz, 1H); MS (DCI/NH3) m/z 247 (M+H)+.

Provenance & Evidence