HCID 67227843, compound → HCID 53251561, compound

HRID 1515752Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-[2-cyclopentyl-1-(3,5-dimethyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (90 mg, 0.28 mmol) and 10% palladium on activated carbon (30 mg) in methanol (200 mL) was heated at 50° C. under hydrogen (50 psi) for 6 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 2-[2-cyclopentyl-1-(3,5-dimethyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (23 mg, 25%): LC/MS m/e calcd for C22H26N [M+H]+ 319.47, observed 319.2; 1H NMR (400 MHz, CDCl3) δ ppm 8.12 (br. s., 1H), 8.05 (d, J=7.8 Hz, 1H), 7.00-7.20 (m, 4H), 6.42 (s, 1H), 5.31 (s, 1H), 4.09 (t, J=7.8 Hz, 1H), 2.08-2.26 (m, 8H), 1.57-1.85 (m, 5H), 1.42-1.53 (m, 2H), 1.14-1.24 (m, 2H).

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-f92e80f080624a2d9796d1bea70d07c7
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

Loading…