HCID 53249983, compound → HCID 58305251, compound

HRID 1515860Notes

Reaction equation

[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](OCC)=[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][CH:11]=[CH:12][CH:13]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture containing 5-[2-cyclopentyl-1-(1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-1H-pyridin-2-one (prepared as in Example 108, 100 mg, 0.33 mmol) and 10% palladium on activated carbon (80 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-pyridin-3-yl-ethyl)-1H-pyrrolo[2,3-b]pyridine (20 mg, 10%): LC/MS m/e calcd for C19H21N3 [M+H]+ 292.40, observed 292; 1H NMR (400 MHz, CDCl3) δ ppm 1.24 (m, 2H), 1.49 (m, 2H), 1.58-1.90 (m, 5H, H), 2.16 (m, 1H), 2.30 (m, 1H), 4.43 (t, J=7.8 Hz, 1H), 6.54 (s, 1H), 7.32 (dd, J=6.1, 7.6 Hz, 1H), 7.48 (m, 1H), 7.97 (d, J=7.8 Hz, 1H), 8.23 (m, 2H), 8.58 (d, J=4.4 Hz, 1H), 8.73 (s, 1H), 12.00 (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-a7849bc08a5747fb9876ac5de89258b5
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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