(2-(trifluoromethyl)phenyl)acetic acid → 1-(1-(4-fluorophenyl)-6,7-dihydro-1H-pyrazolo[4,3-b]pyridin-4(5H)-yl)-2-(2-(trifluoromethyl)phenyl)ethanone

HRID 710623Notes

Reaction equation

HRID 710623 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=O.[F:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[C:30]3[CH2:29][CH2:28][CH2:27][NH:26][C:25]=3[CH:24]=[N:23]2)=[CH:18][CH:17]=1>>[F:15][C:16]1[CH:17]=[CH:18][C:19]([N:22]2[C:30]3[CH2:29][CH2:28][CH2:27][N:26]([C:10](=[O:12])[CH2:9][C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[C:2]([F:1])([F:14])[F:13])[C:25]=3[CH:24]=[N:23]2)=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 594597(2-(trifluoromethyl)phenyl)acetic acidHCID 679846101-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 733354341-(1-(4-fluorophenyl)-6,7-dihydro-1H-pyrazolo[4,3-b]pyridin-4(5H)-yl)-2-(2-(trifluoromethyl)phenyl)ethanoneYield 59%

Procedure

The compound was prepared from 2-trifluoromethylphenylacetic acid and 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine using General Method B. The product mixture was washed with 1 M NaHSO4. The reaction slurry was purified by flash chromatography (SiO2, 24 g column, eluting with 5-50% EtOAc in hexanes) to provide 72 mg (59%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3, mixture of rotamers) δ 8.46 (s, 0.8H), 7.70 (m, 1H), 7.55 (m, 1.2H), 7.41-7.50 (m, 4H), 7.15 (m, 2H), 4.19 (s, 0.3H), 4.06 (s, 1.7H), 3.95 (m, 0.3H), 3.76 (m, 1.7H), 2.82-2.88 (m, 2H), 2.03 (m, 2H); MS: (ES) m/z calculated for C21H18F4N3O [M+H]+ 404.1, found 404.1.

Workup

  1. washThe product mixture was washed with 1 M NaHSO4
  2. customThe reaction slurry was purified by flash chromatography (SiO2, 24 g column, eluting with 5-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e785d61bc3684c579f6ad9d0b48b8c0c
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

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