Methyl iodide → 6-(2-benzyloxy-6-chloro-pyridine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one
Reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([C:17]2[CH:26]=[C:25]([CH3:27])[C:20]3[NH:21][C:22](=[O:24])[O:23][C:19]=3[CH:18]=2)=[O:16])[CH:12]=[C:11]([Cl:28])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH3:30]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([C:17]2[CH:26]=[C:25]([CH3:27])[C:20]3[N:21]([CH3:30])[C:22](=[O:24])[O:23][C:19]=3[CH:18]=2)=[O:16])[CH:12]=[C:11]([Cl:28])[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
4
Procedure
Under a nitrogen atmosphere and while cooling with ice 220 mg (5.06 mmol) sodium hydride (55%, suspension in mineral oil) were added to 2.00 g (5.07 mmol) 6-(2-benzyloxy-6-chloro-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one in 10 mL DMF. The reaction mixture was stirred for 30 min at RT. Then 0.312 mL (5.06 mmol) iodomethane were added and the mixture was stirred overnight at RT. The reaction mixture was poured onto water and the precipitated product was suction filtered, washed with water and dried. The residue was stirred with diethyl ether, suction filtered and dried.