N-Iodosuccinimide → 4-Benzyloxy-1-cyclopropylmethyl-3-iodo-1H-pyridin-2-one
Reaction equation
[I:1]N1C(=O)CCC1=O.[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][N:20]([CH2:23][CH:24]2[CH2:26][CH2:25]2)[C:19](=[O:27])[CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)(=O)C>[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][N:20]([CH2:23][CH:24]2[CH2:25][CH2:26]2)[C:19](=[O:27])[C:18]=1[I:1])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
N-Iodosuccinimide (2.64 g, 11.74 mmol) was added to a solution of intermediate D1 (3.0 g, 11.74 mmol) in acetic acid (40 ml). The reaction mixture was stirred at room temperature for 1 hour, after which it was concentrated in vacuo. The residue was purified by column chromatography (silica gel; DCM as eluent) and finally recrystallized from diethyl ether to yield intermediate D6 (4.12 g, 92%) as a solid.