HCID 67228582, compound → HCID 58305250, compound

HRID 1515865Notes

Reaction equation

[CH:1]1([CH:6]=[C:7]([C:18]2[NH:26][C:21]3=[N:22][CH:23]=[CH:24][CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][N:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].CO>[CH:1]1([CH2:6][CH:7]([C:18]2[NH:26][C:21]3=[N:22][CH:23]=[CH:24][CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][N:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-[2-cyclopentyl-1-(5-methanesulfonyl-pyridin-2-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (84 mg, 0.23 mmol) and 10% palladium on activated carbon (50 mg) in methanol (150 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-(5-methanesulfonyl-pyridin-2-yl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (18 mg, 21%): LC/MS m/e calcd for C20H23N3O2S [M+H]+ 370.49, observed 370.0; 1H NMR (400 MHz, CDCl3) δ ppm 1.17 (m, 2H), 1.47 (m, 2H), 1.61 (m, 3H), 1.77 (m, 2H), 2.25 (m, 2H), 3.08 (s, 3H), 4.44 (t, J=7.7 Hz, 1H), 6.44 (s, 1H), 7.11 (dd, J=4.9, 7.8 Hz, 1H), 7.49 (d, J=8.2 Hz, 1H), 7.95 (d, J=7.8 Hz, 1H), 8.13 (dd, J=2.3 Hz, J=8.2 Hz, 1H), 8.27 (d, J=4.9 Hz, 1H), 9.14 (d, J=2.0 Hz, 1H), 10.97 (br, 1H).

Workup

temperatureAfter cooling to room temperature
customthe catalyst was removed by filtration
washwashed with ethyl acetate
concentrationThe filtrate was concentrated in vacuo
custompurified

Sources & evidence

ORD record: ord-2f8ac6ae6f9544a099ab83be282e9704
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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