HCID 67229394, compound → HCID 53249983, compound

Participants

Reaction Conditions

Reaction Steps

A mixture containing 2-[2-cyclopentyl-1-(6-ethoxy-pyridin-3-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (60 mg, 0.18 mmol) and 10% palladium on activated carbon (60 mg) in methanol (20 mL) was heated at 50° C. under hydrogen (5 atm) 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 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-cyclopentyl-1-(6-ethoxy-pyridin-3-yl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (33 mg, 54%): LC/MS m/e calcd for C21H25N3O [M+H]+ 336.45, observed 336; 1H NMR (400 MHz, CDCl3) δ ppm 1.18 (m, 2H), 1.37 (t, J=7.1 Hz, 3H), 1.47 (m, 2H), 1.62 (m, 2H), 1.68-1.87 (m, 3H), 2.09 (m, 1H), 2.23 (m, 1H), 4.15 (t, J=7.8 Hz, 1H), 4.32 (q, J=7.1 Hz, 2H), 6.32 (s, 1H), 6.65 (d, J=8.6 Hz, 1H), 7.06 (dd, J=5.0, 7.8 Hz, 1H), 7.49 (dd, J=2.1 Hz, J=8.6 Hz, 1H), 7.88 (d, J=7.8 Hz, 1H), 8.13 (m, 2H), 11.47 (s, 1H).

Provenance & Evidence