2-(1-(3-chloro-phenyl)-3-methyl-but-1-enyl)-1H-pyrrolo[2,3-b]pyridine → 2-(1-(3-chloro-phenyl)-3-methyl-butyl)-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(1-(3-chloro-phenyl)-3-methyl-but-1-enyl)-1H-pyrrolo[2,3-b]pyridine (1.3 g, 4.4 mmol) in tetrahydrofuran (50 mL) was treated with platinum dioxide (200 mg). The reaction was stirred at 25° C. under hydrogen atmosphere for 3 d. At this time, the reaction mixture was filtered and the filtrate was concentrated in vacuo. HPLC purification afforded 2-(1-(3-chloro-phenyl)-3-methyl-butyl)-1H-pyrrolo[2,3-b]pyridine (280 mg, 21.4%) as a colorless oil: 1H NMR (300 MHz, d6-DMSO): 6 ppm 11.83 (s, 1H), 8.17 (d, 1H, J=4.8 Hz), 7.96 (d, 1H, J=7.2 Hz), 7.46 (s, 1H), 7.36-7.25 (m, 3H), 7.11 (m, 1H), 6.40 (s, 1H), 4.25 (t, 1H, J=7.8 Hz), 2.11-2.04 (m, 1H), 1.93-1.86 (m, 1H), 1.40-1.36 (m, 1H), 0.91 (s, 3H), 0.88 (s, 3H).

Provenance & Evidence