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

HRID 56237

반응식

HRID 56237 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매4회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-4ac7af751afe4a0c8814018ded4486d1
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434695B2

연결된 노트

불러오는 중…