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

HRID 710624Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 710624
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1.[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:6]4[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:14])[F:13])=[CH:8][CH:7]=4)[C:25]=3[CH:24]=[N:23]2)=[CH:20][CH:21]=1

Komponenten

3

Edukt 2

HCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acidHCID 679846101-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine

Produkt 1

HCID 733353351-(1-(4-fluorophenyl)-6,7-dihydro-1H-pyrazolo[4,3-b]pyridin-4(5H)-yl)-2-(4-(trifluoromethyl)phenyl)ethanoneAusbeute 64 %

Versuchsvorschrift

The compound was prepared from 4-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 77 mg (64%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3, mixture of rotamers) δ 8.45 (s, 0.8H), 7.62 (d, J=7.8 Hz, 2H), 7.55 (s, 0.2H), 7.40-7.49 (m, 4H), 7.15 (m, 2H), 4.08 (s, 0.3H), 3.96 (m, 2H), 3.75 (m, 1.7H), 2.80-2.86 (m, 2H), 2.00 (m, 2H); MS: (ES) m/z calculated for C21H18F4N3O [M+H]+ 404.1, found 404.1.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-86829f1964614da4afd32922a60f81cf
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181241B2

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