Dichloromethane → 1-(4-Methoxy-phenyl)-3-trifluoromethyl-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one

HRID 971133Notes

Reaction equation

[F:1][C:2]([F:16])([F:15])[C:3](Br)=[N:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1.CC[N:19]([CH2:22][CH3:23])CC.[CH2:24](Cl)Cl.CCO[C:30]([CH3:32])=[O:31]>C1(C)C=CC=CC=1>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([N:5]2[C:32]3[C:30](=[O:31])[NH:19][CH2:22][CH2:23][C:24]=3[C:3]([C:2]([F:16])([F:15])[F:1])=[N:4]2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 85 °C

Procedure

Part B. The product from Part A (5.50 g, 41.98 mmol) and 2,2,2-trifluoro-N-(4-methoxyphenyl)-ethanehydrazonoyl bromide (12.90 g, 43.58 mmol) were stirred in toluene (100 mL) at room temperature under N2. Et3N (28.0 mL, 200.1 mmol) was then added. The mixture was stirred at 85° C. for 15 h. It was cooled to room temperature and extracted with EtOAc (3×). The organic layers were washed with H2O (2×) and brine (2×), dried over MgSO4, filtered, and concentrated to dryness. The residue was purified by flash column chromatography (silica gel, CH2Cl2, then CH2Cl2:EtOAc=4:1, then EtOAc) to produce 1-(4-methoxyphenyl)-3-(trifluoromethyl)-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one as a light-tan solid (5.09 g, yield: 39%). LC/MS (ESI+) 312.4 (M+H)+.

Workup

temperatureIt was cooled to room temperature
extractionextracted with EtOAc (3×)
washThe organic layers were washed with H2O (2×) and brine (2×)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated to dryness
customThe residue was purified by flash column chromatography (silica gel, CH2Cl2

Sources & evidence

ORD record: ord-6570251ad94b48ee9ff90b10fa503698
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312214B2

Reaction notes

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