HCID 67229927, compound → HCID 53251559, compound

HRID 1515747Notes

Reaction equation

[CH:1]1([CH:6]=[C:7]([C:17]2[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[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>[Pd].CO>[CH:1]1([CH2:6][CH:7]([C:17]2[CH:18]=[CH:19][C:20]([CH:23]([OH:25])[CH3:24])=[CH:21][CH:22]=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: 50 °C

Procedure

A mixture of 1-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-phenyl}-ethanone (240 mg, 0.72 mmol) and 10% palladium on activated carbon (100 mg) in methanol (200 mL) was heated at 50° C. under hydrogen (50 psi) for 16 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. 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 1-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-ethyl]-phenyl}-ethanol (35 mg, 14%): LC/MS m/e calcd for C22H26N2O [M+H]+ 335.47, observed 335.2; 1H NMR (400 MHz, CD3OD) δ ppm 1.17 (m, 2H), 1.39 (d, J=6.5 Hz, 3H), 1.43 (m, 2H), 1.52-1.85 (m, 5H, H), 2.05 (m, 1H), 2.16 (m, 1H), 4.13 (t, J=7.8 Hz, 1H), 4.77 (q, J=6.5 Hz, 1H), 6.30 (s, 1H), 7.01 (br, 1H), 7.27 (m, 4H), 7.86 (d, J=7.1 Hz, 1H), 8.05 (br, 1H).

Workup

temperatureThe mixture was cooled to room temperature
customthe catalyst was removed by filtration
washwashed with ethyl acetate
concentrationThe filtrate was concentrated in vacuo
customPurification

Sources & evidence

ORD record: ord-00f30a245e3c4e2ba35ddf1840e4e8f2
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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