N-bromobutanimide → Tert-butyl 4-(2-amino-5-bromopyridin-3-yl)-2-fluorobenzoate
Reaction equation
C1C(=O)N([Br:8])C(=O)C1.[NH2:9][C:10]1[C:15]([C:16]2[CH:28]=[CH:27][C:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[C:18]([F:29])[CH:17]=2)=[CH:14][CH:13]=[CH:12][N:11]=1>CC#N>[NH2:9][C:10]1[C:15]([C:16]2[CH:28]=[CH:27][C:19]([C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])=[C:18]([F:29])[CH:17]=2)=[CH:14][C:13]([Br:8])=[CH:12][N:11]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
NBS (2.145 g, 12.05 mmol) was added to a room temperature solution of tert-butyl 4-(2-aminopyridin-3-yl)-2-fluorobenzoate (3.31 g, 11.48 mmol) in MeCN (60 mL). The resulting mixture was stirred for 10 min. The reaction was quenched with 1:1 of sat. aq. Na2S2O3:sat. aq. NaHCO3 solution, and then extracted into ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate and concentrated in vacuo yielding tert-butyl 4-(2-amino-5-bromopyridin-3-yl)-2-fluorobenzoate. The material was used without further purification. LCMS (m/z): 369.0 (MH+), 0.85 min.