2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-methyl-1H-pyrrolo[2,3-b]pyridine → 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-methyl-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-methyl-1H-pyrrolo[2,3-b]pyridine (240 mg, 0.63 mmol) and 10% palladium on activated carbon (100 mg) in methanol (50 mL) was heated at 50° C. under hydrogen (50 psi) for 5 h. After cooling to room temperature, the catalyst was removed by filtration and washed with ethyl acetate. The filtrate was concentrated in vacuo. The residue was purified 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) to afford 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-methyl-1H-pyrrolo[2,3-b]pyridine as a white solid (150 mg, 100%): LC/MS m/e calcd for C22H26N2O2S [M+H]+ 383.53, observed 382.9; 1H NMR (400 MHz, CD3OD) δ ppm 8.21 (s, 1H), 8.06 (s, 1H), 7.87-7.91 (m, J=8.1 Hz, 2H), 7.56-7.61 (m, J=8.3 Hz, 2H), 6.61 (s, 1H), 4.34 (t, J=7.8 Hz, 1H), 2.99-3.10 (m, 3H), 2.48 (s, 3H), 2.22-2.30 (m, 1H), 2.10-2.18 (m, 1H), 1.58-1.86 (m, 5H), 1.43-1.54 (m, 2H), 1.16-1.30 (m, 2H).

Provenance & Evidence