HCID 67229022, compound → HCID 53251872, compound

HRID 1515795Notes

Reaction equation

[CH:1]1([CH:6]=[C:7]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([OH:26])([CH3:25])[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]([C:23]([OH:26])([CH3:24])[CH3:25])=[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 2-{4-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-phenyl}-propan-2-ol (290 mg, 0.84 mmol) and 10% palladium on activated carbon (120 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 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}-propan-2-ol (170 mg, 58%): LC/MS m/e calcd for C23H28N2O [M+H]+ 349.49, observed 349.4; 1H NMR (400 MHz, CD3OD) δ ppm 8.03 (d, J=4.5 Hz, 1H), 7.84 (d, J=7.6 Hz, 1H), 7.38-7.43 (m, J=8.3 Hz, 2H), 7.23-7.28 (m, J=8.1 Hz, 2H), 7.00 (dd, J=7.7, 4.9 Hz, 1H), 6.29 (s, 1H), 4.13 (t, J=7.8 Hz, 1H), 2.02-2.21 (m, 2H), 1.56-1.84 (m, 5H), 1.39-1.51 (m, 8H), 1.12-1.27 (m, 2H).

Workup

temperatureThe mixture was cooled to 25° C.
filtrationthe solids filtered off
washwashed with ethyl acetate
concentrationconcentrated in vacuo
customPurification

Sources & evidence

ORD record: ord-17f1b448156947b1be525a1d66319f98
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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