Potassium tert-butoxide → Tert-butyl 2,4-di-tert-butoxy-5-chloro-6-iodonicotinate
Reaction equation
[Cl:1][C:2]1[C:3]([I:17])=[N:4][C:5](F)=[C:6]([C:14]=1F)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[CH3:18][C:19]([CH3:22])([O-:21])[CH3:20].[K+]>C1COCC1>[C:19]([O:21][C:5]1[N:4]=[C:3]([I:17])[C:2]([Cl:1])=[C:14]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[C:6]=1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])([CH3:22])([CH3:20])[CH3:18]Participants
4
Procedure
Into a solution of tert-butyl 5-chloro-2,4-difluoro-6-iodonicotinate (0.4 g, 1.1 mmol) in THF (2.3 mL) at −78° C. was added a solution of potassium tert-butoxide (1.0 M×2.3 mL, 2.3 mmol). The temperature was allowed to rise to room temperature and the reaction was quenched with saturated NH4Cl. The mixture was extracted with ethyl acetate. The organic layers were combined, dried, evaporated and purified by silica chromatography (0-20% ethyl acetate in hexanes) to give tert-butyl 2,4-di-tert-butoxy-5-chloro-6-iodonicotinate (0.23 g, 44%).