HCID 67229394, compound → HCID 53249983, compound

HRID 1515859Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture containing 2-[2-cyclopentyl-1-(6-ethoxy-pyridin-3-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (60 mg, 0.18 mmol) and 10% palladium on activated carbon (60 mg) in methanol (20 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-(6-ethoxy-pyridin-3-yl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (33 mg, 54%): LC/MS m/e calcd for C21H25N3O [M+H]+ 336.45, observed 336; 1H NMR (400 MHz, CDCl3) δ ppm 1.18 (m, 2H), 1.37 (t, J=7.1 Hz, 3H), 1.47 (m, 2H), 1.62 (m, 2H), 1.68-1.87 (m, 3H), 2.09 (m, 1H), 2.23 (m, 1H), 4.15 (t, J=7.8 Hz, 1H), 4.32 (q, J=7.1 Hz, 2H), 6.32 (s, 1H), 6.65 (d, J=8.6 Hz, 1H), 7.06 (dd, J=5.0, 7.8 Hz, 1H), 7.49 (dd, J=2.1 Hz, J=8.6 Hz, 1H), 7.88 (d, J=7.8 Hz, 1H), 8.13 (m, 2H), 11.47 (s, 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-ec5df67b370648278e8d0ed2b1ad1ed9
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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