Ethyl Acetate → N-(6-(3,5-dichlorophenyl)-1H-indazol-3-yl)butyramide

HRID 497635Notes

Reaction equation

[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:19][C:20]1[CH:21]=[C:22]([C:27]2[CH:35]=[C:34]3[C:30]([C:31]([NH:44][C:45](=[O:49])[CH2:46][CH2:47][CH3:48])=[N:32][N:33]3COCC[Si](C)(C)C)=[CH:29][CH:28]=2)[CH:23]=[C:24]([Cl:26])[CH:25]=1.C(OCC)(=O)C>O1CCCC1>[Cl:19][C:20]1[CH:21]=[C:22]([C:27]2[CH:35]=[C:34]3[C:30]([C:31]([NH:44][C:45](=[O:49])[CH2:46][CH2:47][CH3:48])=[N:32][NH:33]3)=[CH:29][CH:28]=2)[CH:23]=[C:24]([Cl:26])[CH:25]=1

Participants

Conditions

Temperature: 65 °C

Procedure

11.2 cm3 of tetrabutylammonium fluoride as a 1M solution in tetrahydrofuran are added to 1 g of N-[6-(3,5-dichlorophenyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide, described 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 75 cm3 of ethyl acetate. The organic phase is washed with 2×50 cm3 of saturated aqueous sodium hydrogen carbonate solution and then with 50 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.), 290 mg of N-[6-(3,5-dichlorophenyl)-1H-indazol-3-yl]butanamide are obtained in the form of a white product.

Workup

washThe organic phase is washed with 2×50 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.), 290 mg of N-[6-(3,5-dichlorophenyl)-1H-indazol-3-yl]butanamide
customare obtained in the form of a white product

Sources & evidence

ORD record: ord-9fdf3097c5e74ccca04d34f4aede8a58
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949579B2

Reaction notes

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