Bromine → HCID 91385505, compound

Reaction equation

[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([O:15][C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][N:17]=2)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[S-:24][C:25]#[N:26].[K+].BrBr>C(O)(=O)C>[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([O:15][C:16]2[N:17]=[C:18]3[S:24][C:25]([NH2:26])=[N:22][C:19]3=[CH:20][CH:21]=2)[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Procedure

To a solution of tert-butyl{3-[(5-aminopyridin-2-yl)oxy]-4-fluorophenyl}carbamate (2.50 g, 7.8 mmol) and potassium thiocyanate (2.92 g, 30 mmol) in acetic acid (30 mL) was added dropwise bromine (1.93 g, 12 mmol) under ice-cooling, and the mixture was stirred at room temperature overnight. The yellow insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. To the residue was added saturated aqueous sodium hydrogen carbonate solution (100 mL), and the mixture was extracted with ethyl acetate (100 mL×2). The ethyl acetate layers were combined, and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was triturated with diethyl ether to give the title compound (1.92 g, 65%) as a pale-yellow amorphous.