Methanol → HCID 86654512, compound

HRID 1515792Notes

Reaction equation

[CH:1]1([CH:6]=[C:7]([C:17]2[CH:22]=[CH:21][C:20]([C:23](=O)C)=[CH:19][CH:18]=2)[C:8]2[NH:16][C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:26][OH:27]>[Pd]>[CH:1]1([CH2:6][CH:7]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH:26]=[O:27])=[CH:19][CH:18]=2)[C:8]2[NH:16][C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture 1-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-phenyl}-ethanone (prepared as in Example 64, 280 mg, 0.84 mmol) and 10% palladium on activated carbon (56 mg) in methanol (200 mL) was heated at 50° C. under hydrogen (50 psi) for 5 h. The mixture was cooled to 25° C., the solids 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-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-phenyl}-ethanone (100 mg, 35%): LC/MS m/e calcd for C22H24N2O [M+H]+ 333.45, observed 333.1; 1H NMR (400 MHz, CD3OD) δ ppm 8.06 (d, J=4.5 Hz, 1H), 7.85-7.95 (m, 3H), 7.45 (d, J=7.6 Hz, 2H), 6.99-7.05 (m, 1H), 6.35 (s, 1H), 4.25 (t, J=7.8 Hz, 1H), 2.56 (s, 3H), 2.24 (dt, J=13.6, 7.0 Hz, 1H), 2.09 (dt, J=13.6, 7.0 Hz, 1H), 1.57-1.85 (m, 5H), 1.41-1.54 (m, 2H), 1.13-1.27 (m, 2H).

Workup

filtrationthe solids filtered off
washwashed with ethyl acetate
concentrationconcentrated in vacuo
customPurification

Sources & evidence

ORD record: ord-b2850c48ece7490aacc18d000380be0b
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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