反应详情

温度

50 °C

A mixture of (Z)-2-[2-(1,4-dioxa-spiro[4.4]non-7-yl)-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (enantiomer 1, prepared as in Example 78, 140 mg, 0.33 mmol) and 10% palladium on activated carbon (50 mg) in methanol (125 mL) was heated at 50° C. under hydrogen (50 psi) for 96 h. The mixture was cooled to 25° C., the catalyst was 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 0.05% trifluoroacetic acid in water) afforded 3-[2-(4-methanesulfonyl-phenyl)-2-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-cyclopentanone (diastereomer 1, 8 mg, 6%): LC/MS m/e calcd for C21H22N2O3S [M+H]+ 383.49, observed 383.0; 1H NMR (400 MHz, CD3OD) δ ppm 8.09 (d, J=4.5 Hz, 1H), 7.90 (d, J=7.8 Hz, 2H), 7.63 (d, J=7.8 Hz, 2H), 7.05 (dd, J=7.7, 4.9 Hz, 1H), 6.43 (d, J=3.0 Hz, 1H), 4.75-4.84 (m, 1H), 4.59 (br. s., 1H), 4.38 (t, J=7.8 Hz, 1H), 3.08 (s, 2H), 2.37-2.49 (m, 1H), 2.05-2.30 (m, 4H), 1.88-1.99 (m, 1H), 1.58-1.71 (m, 1H), 1.22-1.38 (m, 1H), 0.90 (t, J=6.6 Hz, 1H).

1. temperatureThe mixture was cooled to 25° C.
2. filtrationthe catalyst was filtered off
3. washwashed with ethyl acetate
4. concentrationconcentrated in vacuo
5. customPurification