Ammonium formate → ethyl 3-(6-amino-1H-benzimidazol-1-yl)-3-phenylpropanoate

HRID 1676018ノート

反応式

HRID 1676018 の反応式
[CH2:1]([O:3][C:4](=[O:25])[CH:5]=[C:6]([N:13]1[C:17]2[CH:18]=[CH:19][C:20]([N+:22]([O-])=O)=[CH:21][C:16]=2[N:15]=[CH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].[CH2:26]([O:28][C:29](=[O:50])[CH:30]=[C:31]([N:38]1[C:42]2[CH:43]=[C:44]([N+:47]([O-])=O)[CH:45]=[CH:46][C:41]=2[N:40]=[CH:39]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH3:27].C([O-])=O.[NH4+]>C(O)C.O.[Pd]>[NH2:47][C:44]1[CH:45]=[CH:46][C:41]2[N:40]=[CH:39][N:38]([CH:31]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:30][C:29]([O:28][CH2:26][CH3:27])=[O:50])[C:42]=2[CH:43]=1.[NH2:22][C:20]1[CH:19]=[CH:18][C:17]2[N:13]([CH:6]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:25])[CH:14]=[N:15][C:16]=2[CH:21]=1

参加物

8

反応物 3

HCID 2723923Ammonium formateHCID 67352746Ethyl-3-(5-nitro-1h-benzimidazol-1-yl)-3-phenyl-2-propenoateHCID 67353774Ethyl-3-(6-nitro-1h-benzimidazol-1-yl)-3-phenyl-2-propenoate

生成物 2

HCID 67351765ethyl 3-(6-amino-1H-benzimidazol-1-yl)-3-phenylpropanoateHCID 67351926ethyl 3-(5-amino-1H-benzimidazol-1-yl)-3-phenylpropanoate

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a mixture of ethyl-3-(5-nitro-1H-benzimidazol-1-yl)-3-phenyl-2-propenoate and ethyl-3-(6-nitro-1H-benzimidazol-1-yl)-3-phenyl-2-propenoate (5.34 g, 15.8 mmol) in a mixture of ethanol and water (10:1, 66 mL) was added palladium on carbon (801 mg, 10% w/w Pd) and ammonium formate (6.0 g, 95 mmol). The suspension was heated to reflux, and was stirred at this temperature for 1.5 hours. The reaction mixture was allowed to cool to room temperature, then filtered through Celite®, and the filter pad washed several times with ethanol. The combined filtrates were evaporated in vacuo, and the residue was purified by flash column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (99:1) to give, in order of elution, ethyl 3-(6-amino-1H-benzimidazol-1-yl)-3-phenylpropanoate, [LCMS (Method A, Mobile Phase I) RT=3.33 min, MH+ 310] and ethyl 3-(5-amino-1H-benzimidazol-1-yl)-3-phenylpropanoate (1.96 g), [LCMS (Method A, Mobile Phase I) RT=3.35 min, MH+ 310].

後処理

  1. temperatureThe suspension was heated
  2. temperatureto reflux
  3. filtrationfiltered through Celite®
  4. washthe filter pad washed several times with ethanol
  5. customThe combined filtrates were evaporated in vacuo
  6. customthe residue was purified by flash column chromatography on silica gel
  7. washeluting with a mixture of dichloromethane and methanol (99:1)

出典と根拠

ORDレコード
ord-311afd4a87b14749aa867a06227778b2
出典データセット
uspto-grants-2011_08
特許番号
US08003806B2

反応ノート

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