Ethyl Acetate → N-(6-(4-chlorophenyl)-1H-indazol-3-yl)butyramide

HRID 497638Notes

Reaction equation

[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:34]=[C:33]3[C:29]([C:30]([NH:43][C:44](=[O:48])[CH2:45][CH2:46][CH3:47])=[N:31][N:32]3COCC[Si](C)(C)C)=[CH:28][CH:27]=2)=[CH:22][CH:21]=1.C(OCC)(=O)C>O1CCCC1>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:34]=[C:33]3[C:29]([C:30]([NH:43][C:44](=[O:48])[CH2:45][CH2:46][CH3:47])=[N:31][NH:32]3)=[CH:28][CH:27]=2)=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 65 °C

Procedure

9.5 cm3 of tetrabutylammonium fluoride as a 1M solution in tetrahydrofuran are added to a solution of 600 mg of N-[6-(4-chlorophenyl)-1-[[2-(trimethylsilyl)ethoxy]-methyl]-1H-indazol-3-yl]butanamide, prepared previously, in 20 cm3 of tetrahydrofuran, the reaction medium is then heated at about 65° C. for 18 hours and the heating is stopped to add 40 cm3 of ethyl acetate. The organic phase is washed with 2×30 cm3 of saturated aqueous sodium hydrogen carbonate solution and then with 30 cm3 of saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulphate, filtered and evaporated under reduced pressure (2 kPa; 50° C.). After drying (90 Pa; 50° C.), 238 mg of N-[6-(4-chlorophenyl)-1H-indazol-3-yl]butanamide are obtained in the form of a beige-coloured powder.

Workup

washThe organic phase is washed with 2×30 cm3 of saturated aqueous sodium hydrogen carbonate solution
dry with materialThe organic phase is dried over magnesium sulphate
filtrationfiltered
customevaporated under reduced pressure (2 kPa; 50° C.)
dry with materialAfter drying (90 Pa; 50° C.), 238 mg of N-[6-(4-chlorophenyl)-1H-indazol-3-yl]butanamide
customare obtained in the form of a beige-coloured powder

Sources & evidence

ORD record: ord-63672352fcf84c4381ac2a9805e1c63d
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949579B2

Reaction notes

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