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

HRID 710626Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 710626
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([OH:15])=O)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].[F:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[C:31]3[CH2:30][CH2:29][CH2:28][NH:27][C:26]=3[CH:25]=[N:24]2)=[CH:19][CH:18]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([N:27]2[CH2:28][CH2:29][CH2:30][C:31]3[N:23]([C:20]4[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=4)[N:24]=[CH:25][C:26]2=3)=[O:15])[CH:5]=[CH:6][C:7]=1[C:8]([F:9])([F:10])[F:11]

Komponenten

3

Edukt 2

HCID 573679893-Chloro-4-(trifluoromethyl)phenylacetic acidHCID 679846101-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridine

Produkt 1

HCID 733354362-(3-chloro-4-(trifluoromethyl)phenyl)-1-(1-(4-fluorophenyl)-6,7-dihydro-1H-pyrazolo[4,3-b]pyridin-4(5H)-yl)ethanoneAusbeute 52 %

Versuchsvorschrift

The compound was from prepared from 3-chloro-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 brine and 2×1 M NaHSO4. The reaction slurry was purified by flash chromatography (SiO2, 24 g column, eluting with 5-60% EtOAc in hexanes) to provide 68 mg (52%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3, mixture of rotamers) δ 8.45 (s, 0.8H), 7.67 (m, 1H), 7.55 (s, 0.2H), 7.44-7.49 (m, 3H), 7.30 (m, 1H), 7.14-7.21 (m, 2H), 4.04 (s, 0.4H), 3.94 (m, 0.4H), 3.92 (s, 1.6H), 3.77 (m, 1.6H), 2.82-2.87 (m, 2H), 2.04 (m, 2H); MS: (ES) m/z calculated for C21H17ClF4N3O [M+H]+ 438.1, found 438.1.

Aufarbeitung

  1. washThe product mixture was washed with brine and 2×1 M NaHSO4
  2. customThe reaction slurry was purified by flash chromatography (SiO2, 24 g column, eluting with 5-60% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-deef0f3e898e4fc4996704b5e2f3165c
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181241B2

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