HCID 53249983, compound → HCID 58305251, compound

Participants

Reaction Conditions

Reaction Steps

A mixture containing 5-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-1H-pyridin-2-one (prepared as in Example 108, 100 mg, 0.33 mmol) and 10% palladium on activated carbon (80 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-pyridin-3-yl-ethyl)-1H-pyrrolo[2,3-b]pyridine (20 mg, 10%): LC/MS m/e calcd for C19H21N3 [M+H]+ 292.40, observed 292; 1H NMR (400 MHz, CDCl3) δ ppm 1.24 (m, 2H), 1.49 (m, 2H), 1.58-1.90 (m, 5H, H), 2.16 (m, 1H), 2.30 (m, 1H), 4.43 (t, J=7.8 Hz, 1H), 6.54 (s, 1H), 7.32 (dd, J=6.1, 7.6 Hz, 1H), 7.48 (m, 1H), 7.97 (d, J=7.8 Hz, 1H), 8.23 (m, 2H), 8.58 (d, J=4.4 Hz, 1H), 8.73 (s, 1H), 12.00 (br, 1H).

Provenance & Evidence