Water → 3-(1-Methyl-4-piperidinyl)-1-[3-(trifluoromethyl)phenyl]-1H-indazole

HRID 986147

Reaction equation

[H-].[Na+].[CH3:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][N:11]=2)[CH2:6][CH2:5]1.F[C:20]1[CH:21]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:24][CH:25]=1.O>CN(C)C=O>[CH3:3][N:4]1[CH2:5][CH2:6][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[N:11]=2)[CH2:8][CH2:9]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred suspension of 4.9 g of a 50% oil dispersion of sodium hydride in 60 ml of dimethylformamide was added dropwise a solution a 10.0 g of 3-(1-methyl-4-piperidinyl)-1H-indazole in 80 ml of hot dimethylformamide. The reaction mixture was stirred for 1 hr and then 15.2 g of 3-fluorobenzotrifluoride was added. The reaction was heated at 90° C. for 22 hrs, cooled and poured into water. The aqueous mixture was extracted with ether. The ethereal extracts were dried over anhydrous magnesium sulfate and concentrated to give an oil. The oil was flash chromatographed (silica gel, diethylamine-ethyl acetate (1:9)). Evaporation of the appropriate fractions followed by recrystallization twice from hexane yielded 2.96 g (18%) of product, mp 103°-105° C.

Workup

temperaturecooled
extractionThe aqueous mixture was extracted with ether
dry with materialThe ethereal extracts were dried over anhydrous magnesium sulfate
concentrationconcentrated
customto give an oil
customchromatographed (silica gel, diethylamine-ethyl acetate (1:9))
customEvaporation of the appropriate fractions
customfollowed by recrystallization twice from hexane

Sources & evidence

ORD record: ord-c08c174e0c274b8c8c9e78246466894a
Source dataset: uspto-grants-1987_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04710573

Linked notes

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