2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-N,N-dimethyl-acetamide → 2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-N,N-dimethyl-acetamide

Participants

Reaction Steps

A mixture of 2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-N,N-dimethyl-acetamide (276 mg, 0.59 mmol) and 10% palladium on activated carbon (50.0 mg) in methanol (200 mL) was heated at 50° C. under 50 bar of hydrogen in a steel bomb pressure for 6 h. The mixture was then cooled to room temperature. The catalyst was removed by filtration and washed with ethyl acetate. The filtrate was concentrated in vacuo and 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-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-N,N-dimethyl-acetamide (140 mg, 50.7%) as a white solid: LC/MS m/e calcd for C25H31N3O4S [M+H]+ 470.61, observed 470.2. solid 1H NMR (400 MHz, CD3OD) δ ppm 7.86-7.93 (m, 4H), 7.59 (d, J=8.1 Hz, 3H), 7.52 (s, 1H), 6.32 (s, 1H), 4.84 (s, 2H), 4.28 (t, J=7.8 Hz, 1H), 3.08 (s, 3H), 3.10 (s, 3H), 2.98 (s, 3H), 2.22-2.30 (m, 1H), 2.03-2.13 (m, 2H), 1.61-1.79 (m, 4H), 1.48 (br. s., 1H), 1.21-1.23 (m, 1H).

Provenance & Evidence