HCID 67228295, compound → 2-[2-cyclopentyl-1-(4-isopropyl-phenyl)-ethyl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-{4-[2-cyclopentyl-1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-phenyl}-propan-2-ol (prepared as in Example 119, 150 mg, 0.41 mmol) and 10% palladium on activated carbon (0.2 g) 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-isopropyl-phenyl)-ethyl]-5-fluoro-1H-pyrrolo[2,3-b]pyridine as a white solid (5.7 mg, 4%): LC/MS m/e calcd for C23H27FN2 [M+H]+ 351.48, observed 351.26; 1H NMR (400 MHz, CD3OD) δ ppm 1.19 (m, 2H), 1.22 (d, J=6.8 Hz, 6H), 1.48 (m, 2H), 1.57-1.87 (m, 5H, H), 2.06 (m, 1H), 2.17 (m, 1H), 2.86 (m, 1H), 4.11 (t, J=7.8 Hz, 1H), 6.29 (s, 1H), 7.16 (d, J=8.3 Hz, 2H), 7.22 (d, J=8.3 Hz, 2H), 7.60 (dd, J=2.5 Hz, 3JHF=9.2 Hz, 1H), 7.95 (brm, 1H).

Provenance & Evidence