Potassium Carbonate → 1-Phenyl-1H-indole-5-carbaldehyde

HRID 84184

反応式

HRID 84184 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12]C)=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.I[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:15]1([N:1]2[C:9]3[C:4](=[CH:5][C:6]([CH:10]=[O:12])=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 2737635methyl 1H-indole-5-carboxylate

生成物 1

HCID 206209271-Phenyl-1H-indole-5-carbaldehyde収率 28.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The suspension of methyl indole-5-carboxylate (4) (0.70 g, 4.82 mmol), 4-iodobenzene (0.65 mL, 5.79 mmol), K2CO3 (0.93 g, 6.75 mmol), CuO (0.04 g, 0.48 mmol) in DMF (2 mL) was refluxed for 2 days. The reaction mixture was quenched with water, followed by extraction with EtOAc (20 mL×3). The combined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure to give a yellow residue, which was purified by silica gel chromatography (EtOAc:n-hexane=1:4) to afford 6 (0.30 g). 1H NMR (500 MHz, CD3OD): δ 6.83 (d, J=3.2 Hz, 1H), 7.431-7.44 (m, 1H), 7.42 (d, J=3.1 Hz, 1H), 7.49-7.51 (m, 2H), 7.54-7.60 (m, 3H), 7.77 (dd, J=8.7, 1.1 Hz, 1H), 10.06 (s, 1H).

後処理

  1. temperaturewas refluxed for 2 days
  2. customThe reaction mixture was quenched with water
  3. extractionfollowed by extraction with EtOAc (20 mL×3)
  4. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customto give a yellow residue, which
  7. customwas purified by silica gel chromatography (EtOAc:n-hexane=1:4)

出典と根拠

ORDレコード
ord-09833f19478744b7ac5f80489f28ba4c
出典データセット
uspto-grants-2014_09
特許番号
US08846748B2

関連ノート

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