HCID 67227773, compound → 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-isopropoxy-1H-pyrrolo[2,3-b]pyridine

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Reaction Steps

A mixture of 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-isopropoxy-1H-pyrrolo[2,3-b]pyridine (236 mg, 0.55 mmol) and 10% palladium on activated carbon (40 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 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-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-5-isopropoxy-1H-pyrrolo[2,3-b]pyridine (180 mg, 76%) as a white solid: LC/MS m/e calcd for C24H30N2O3S [M+H]+ 427.58, observed 427.2; 1H NMR (400 MHz, CD3OD) δ ppm 7.88-7.92 (m, J=8.3 Hz, 2H), 7.81 (d, J=2.3 Hz, 1H), 7.58-7.63 (m, J=8.3 Hz, 2H), 7.51 (d, J=2.5 Hz, 1H), 6.33 (s, 1H), 4.53 (dt, J=12.1, 6.1 Hz, 1H), 4.30 (t, J=7.8 Hz, 1H), 3.10 (s, 3H), 2.24-2.32 (m, 1H), 2.07-2.15 (m, 1H), 1.61-1.88 (m, 5H), 1.46-1.57 (m, 2H), 1.18-1.35 (m, 8H).

Provenance & Evidence