Diiodomethane → 3-((6-nitro-1H-indol-1-yl)methoxy)benzonitrile

HRID 56237

反応式

HRID 56237 の反応式
[H-].[Na+].[N+:3]([C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[CH:11][NH:12]2)=[CH:8][CH:7]=1)([O-:5])=[O:4].[OH:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[C:19]#[N:20].I[CH2:25]I>CN(C=O)C>[N+:3]([C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[CH:11][N:12]2[CH2:25][O:15][C:16]2[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=2)[C:19]#[N:20])=[CH:8][CH:7]=1)([O-:5])=[O:4]

参加物

6

反応物 4

HCID 6346DiiodomethaneHCID 133943-CyanophenolHCID 24758Sodium hydrideHCID 785026-Nitro-1H-indole

生成物 1

HCID 900304473-((6-nitro-1H-indol-1-yl)methoxy)benzonitrile収率 51%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒4 回

実験手順

To a mixture of NaH (3.0 g, 75.0 mmol, 60%) in DMF (20 mL) were added a solution of 6-nitro-1H-indole (4.86 g, 30.0 mmol) in DMF (10 mL) and a solution of 3-hydroxybenzonitrile (3.57 g, 30.0 mmol) in DMF (10 mL) at 0° C. and the mixture was stirred at rt for 2 h. To the reaction mixture was added a solution of diiodomethane (7.5 mL, 90.0 mmol) in DMF (10 mL) slowly without light and the mixture was stirred at rt for 20 h. The mixture was then quenched with water and filtered. The filtrate was extracted with DCM (30 mL×6) and the combined organic layers were washed with brine (50 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a yellow solid (4.47 g, 51%).

後処理

  1. customThe mixture was then quenched with water
  2. filtrationfiltered
  3. extractionThe filtrate was extracted with DCM (30 mL×6)
  4. washthe combined organic layers were washed with brine (50 mL×3)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

出典と根拠

ORDレコード
ord-4ac7af751afe4a0c8814018ded4486d1
出典データセット
uspto-grants-2016_09
特許番号
US09434695B2

関連ノート

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