HCID 67229927, compound → HCID 53251559, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-phenyl}-ethanone (240 mg, 0.72 mmol) and 10% palladium on activated carbon (100 mg) in methanol (200 mL) was heated at 50° C. under hydrogen (50 psi) for 16 h. The mixture was cooled to room temperature, the catalyst was removed by filtration and washed with ethyl acetate. The filtrate was concentrated in vacuo. Purification using a Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 1-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-phenyl}-ethanol (35 mg, 14%): LC/MS m/e calcd for C22H26N2O [M+H]+ 335.47, observed 335.2; 1H NMR (400 MHz, CD3OD) δ ppm 1.17 (m, 2H), 1.39 (d, J=6.5 Hz, 3H), 1.43 (m, 2H), 1.52-1.85 (m, 5H, H), 2.05 (m, 1H), 2.16 (m, 1H), 4.13 (t, J=7.8 Hz, 1H), 4.77 (q, J=6.5 Hz, 1H), 6.30 (s, 1H), 7.01 (br, 1H), 7.27 (m, 4H), 7.86 (d, J=7.1 Hz, 1H), 8.05 (br, 1H).

Provenance & Evidence