HCID 67228648, compound → HCID 53250742, compound

HRID 1515645Notes

Reaction equation

[CH:1]1([CH:6]=[C:7]([C:18]2[NH:28][C:21]3=[N:22][CH:23]=[C:24]([O:26][CH3:27])[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].CO>[CH:1]1([CH2:6][CH:7]([C:18]2[NH:28][C:21]3=[N:22][CH:23]=[C:24]([O:26][CH3:27])[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-[2-cyclopentyl-1-(4-trifluoromethyl-phenyl)-vinyl]-5-methoxy-1H-pyrrolo[2,3-b]pyridine (191 mg, 0.49 mmol) and 10% palladium on activated carbon (50 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 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-(4-trifluoromethyl-phenyl)-ethyl]-5-methoxy-1H-pyrrolo[2,3-b]pyridine (80 mg, 41.9%) as a white solid: LC/MS m/e calcd for C22H23F3N2O [M+H]+ 389.54, observed 389.3; 1H NMR (400 MHz, CD3OD) δ ppm 7.84 (d, J=2.5 Hz, 1H), 7.61 (d, J=8.1 Hz, 2H), 7.52 (d, J=8.6 Hz, 3H), 6.31 (s, 1H), 4.25 (t, J=8.0 Hz, 1H), 3.86 (s, 3H), 2.22-2.30 (m, 1H), 2.05-2.13 (m, 1H), 1.60-1.87 (m, 6H), 1.44-1.57 (m, 2H), 1.17-1.29 (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
custompurified

Sources & evidence

ORD record: ord-702dfcf682bf45b587147fdc55203d8a
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

Loading…