HCID 53251717, compound → HCID 53251718, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-[(E)-1-(4-methanesulfonyl-phenyl)-3,3-dimethyl-but-1-enyl]-1H-pyrrolo[2,3-b]pyridine (prepared as in Example 73, 40 mg, 0.11 mmol) and 10% palladium on activated carbon (12 mg) in methanol (250 mL) was heated at 50° C. under hydrogen (50 psi) for 16 h. The mixture was cooled to 25° C., the catalyst filtered off, washed with ethyl acetate and concentrated in vacuo. Purification 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) afforded 2-[1-(4-methanesulfonyl-phenyl)-3,3-dimethyl-butyl]-1H-pyrrolo[2,3-b]pyridine (10 mg, 25%) as a white solid: LC/MS m/e calcd for C20H24N2O2S [M+H]+ 357.49, observed 357.4; 1H NMR (400 MHz, CD3OD) δ ppm 8.09 (br. s., 1H), 7.84-7.93 (m, 3H), 7.65 (d, J=8.3 Hz, 2H), 7.05 (dd, J=7.7, 4.9 Hz, 1H), 6.43 (s, 1H), 4.41-4.47 (m, 1H), 3.04-3.15 (m, 3H), 2.40 (dd, J=14.0, 7.7 Hz, 1H), 1.99-2.06 (m, 1H), 0.91 (s, 9H).

Provenance & Evidence