Potassium Carbonate → 2-(4-oxiranylmethylpiperazin-1-yl)-1-phenyl-1H-indole-3-carboxaldehyde

HRID 1678143ノート

反応式

HRID 1678143 の反応式
[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH:16]=[O:17])=[C:8]2[N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:24]([CH:26]1[O:28][CH2:27]1)Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[O:28]1[CH2:27][CH:26]1[CH2:24][N:21]1[CH2:22][CH2:23][N:18]([C:8]2[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:15]3[C:10]([C:9]=2[CH:16]=[O:17])=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:19][CH2:20]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 539968311-Phenyl-2-piperazin-1-yl-1H-indole-3-carboxaldehyde

生成物 1

HCID 114852322-(4-oxiranylmethylpiperazin-1-yl)-1-phenyl-1H-indole-3-carboxaldehyde収率 41%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A stirred mixture of 1-phenyl-2-(piperazin-1-yl)-1H-indole-3-carboxaldehyde (438 mg, 1.37 mmol), epibromohydrin (188 mg, 1.37 mmol), potassium carbonate (758 mg, 5.49 mmol) and acetonitrile (20 ml) is heated at reflux for 2.5 hr. The reaction is cooled and the solids are removed by filtration. The filtrate is concentrated and the residue is purified by chromatography eluting with dichloromethane-1 to 5% methanol. Fractions containing the desired product are combined and concentrated to afford 2-(4-oxiranylmethylpiperazin-1-yl)-1-phenyl-1H-indole-3-carboxaldehyde (41% yield) as a yellow solid. LC/MS: MS 376 (M+H); RT 2.65 min; NMR (CDCl3): 10.28 (1H, s), 8.26 (1H, d), 7.43-7.65 (3H, m), 7.17-7.42 (3H, m), 7.13 (1H, t), 6.96 (1H, d), 3.49 (4H, m), 3.03 (1H, m), 2.56-2.86 (4H, m), 2.30-2.50 (2H, m), 1.74 (2H, m), 1.56 (2H, s).

後処理

  1. temperatureis heated
  2. temperatureat reflux for 2.5 hr
  3. temperatureThe reaction is cooled
  4. customthe solids are removed by filtration
  5. concentrationThe filtrate is concentrated
  6. customthe residue is purified by chromatography
  7. washeluting with dichloromethane-1 to 5% methanol
  8. additionFractions containing the desired product
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-ebc7bca11a434806b3290dd610c2f33b
出典データセット
uspto-grants-2011_08
特許番号
US08008491B2

反応ノート

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