Butyryl chloride → N-[4-iodo-1H-indazol-3-yl]butanamide
Reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[I:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10]([NH2:17])=[N:11][NH:12]2>N1C=CC=CC=1>[I:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[C:10]([NH:17][C:1](=[O:5])[CH2:2][CH2:3][CH3:4])=[N:11][NH:12]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
0.20 cm3 of butyryl chloride is added to 500 mg of 4-iodo-1H-indazole-3-amine, described previously, in 15 cm3 of pyridine, and cooled to about 5° C. The reaction medium is allowed to return to about 19° C. over 50 hours. The reaction medium is evaporated under reduced pressure (2 kPa; 50° C.). The residue is taken up in 15 cm3 of ethyl acetate, 15 cm3 of tetrahydrofuran and 15 cm3 of distilled water. The organic phase is dried over magnesium sulphate and then filtered through a sinter funnel and evaporated under reduced pressure (2 kPa; 50° C.). The residue is taken up in 15 cm3 of dichloromethane and filtered. The insoluble material is taken up in 10 cm3 of methanol and filtered off and the filtrate is evaporated under reduced pressure, to give after drying (90 Pa; 50° C.), 70 mg of N-[4-iodo-1H-indazol-3-yl]butanamide in the form of an off-white solid.