HCID 67228577, compound → HCID 58305247, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-6-methoxy-1H-pyrrolo[2,3-b]pyridine (0.22 g, 0.56 mmol) and 10% palladium on activated carbon (0.2 g) in methanol (150 mL) was heated at 50° C. under hydrogen (50 psi) for 12 h. After cooling to room temperature, the catalyst was removed by filtration and washed with ethyl acetate. The filtrate was concentrated in vacuo to give a residue which 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]-6-methoxy-1H-pyrrolo[2,3-b]pyridine (18 mg, 8.2%) as a white solid: LC/MS m/e calcd for C22H26N2O3S [M+H]+ 399.53, observed 399.3; 1H NMR (400 MHz, CDCl3) δ ppm 1.16 (m, 2H), 1.48 (m, 2H), 1.56-1.85 (m, 5H, H), 2.04 (m, 1H), 2.17 (m, 1H), 3.05 (s, 3H), 3.90 (s, 3H), 4.14 (t, J=7.7 Hz, 1H), 6.29 (s, 1H), 6.55 (d, J=8.5 Hz, 1H), 7.42 (d, J=8.1 Hz, 2H), 7.73 (d, J=8.5 Hz, 1H), 7.86 (d, J=8.1 Hz, 2H), 8.31 (s, 1H).

Provenance & Evidence