Acetic Acid → 5-(Benzoxazol-2-yl)-1-(3-methoxycarbonylphenylmethyl)-2-methylbenzimidazole
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH2:11][NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[O:20][C:21]4[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=4[N:23]=3)=[CH:15][C:14]=2[N+:28]([O-])=O)[CH:8]=[CH:9][CH:10]=1)=[O:4].[C:31](O)(=O)[CH3:32]>[Fe]>[O:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[C:19]1[C:16]1[CH:17]=[CH:18][C:13]2[N:12]([CH2:11][C:7]3[CH:8]=[CH:9][CH:10]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=3)[C:31]([CH3:32])=[N:28][C:14]=2[CH:15]=1Participants
4
Procedure
To 2-(2-(3-methoxycarbonylphenylmethyl)aminonitrobenzen-5-yl)benzoxazole (see Working Example 117-1) (220 mg, 0.545 mmol) was added iron powder (91.4 mg, 1.64 mmol) and acetic acid (5 mL), and this was heated to reflux for 12 hours. After the reaction solution was cooled, it was concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (139 mg, 64% yield) as white crystals.