Methanol → HCID 71074609、化合物

HRID 1851890ノート

反応式

HRID 1851890 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=1.[H-].[Na+].CO>CN(C=O)C>[Br:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:1]2[C:9]3[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)=[CH:17][CH:18]=1

参加物

6

反応物 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromideHCID 2737635methyl 1H-indole-5-carboxylate

生成物 1

HCID 71074609HCID 71074609、化合物収率 52%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of methyl 1H-indole-5-carboxylate (1.09 g, 6.2 mmol, 1 equiv) and 1-(bromomethyl)-4-bromobenzene (1.70 g, 6.82 mmol, 1.1 equiv) in anhydrous DMF (30 mL) under argon atmosphere was added sodium hydride (500 mg, 12.4 mmol, 2 equiv) in small portions. The mixture was stirred 2 h at room temperature. The reaction mixture was then neutralized by addition of methanol and concentrated in vacuo. The residue was dissolved in AcOEt, washed with brine and dried over MgSO4. The crude was purified by flash chromatography (Hexane/AcOEt 7.5/2.5) to afford the title compound as a white powder (1.09 g, 3.2 mmol, 52%). ESI-MS (m/z): 344/346 [M+H]+.

後処理

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in AcOEt
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. customThe crude was purified by flash chromatography (Hexane/AcOEt 7.5/2.5)

出典と根拠

ORDレコード
ord-4d1788964f6b4b03baaeed9e21b9a512
出典データセット
uspto-grants-2015_02
特許番号
US08957093B2

反応ノート

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