Benzyl Bromide → 1-Benzyl-6-bromo-1H-indole-3-carbaldehyde

HRID 337612

반응식

HRID 337612 반응식
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C>[CH2:15]([N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:10]=2)[C:6]([CH:11]=[O:12])=[CH:7]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 27948306-Bromoindole-3-carbaldehyde

생성물 1

HCID 866516751-Benzyl-6-bromo-1H-indole-3-carbaldehyde

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

6-Bromo-1H-indole-3-carbaldehyde (1 eq.) from the previous step was dissolved in DMF (0.19 M). Sodium hydride was added (1.5 eq.) and the resulting solution was stirred at RT for 20 min. Benzyl bromide (1 eq.) was then added and the reaction solution was allowed to stir at RT for 24 h. The reaction mixture was subsequently quenched with water and extracted with EtOAc. The combined organic extracts were dried over MgSO4. Filtration and concentration of the filtrate in vacuo afforded a yellow oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 4:1 (v/v) Hex:EtOAc 3:7 (v/v) Hex:EtOAc) afforded the title compound as a yellow solid.

후처리

  1. stirringto stir at RT for 24 h
  2. customThe reaction mixture was subsequently quenched with water
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationFiltration and concentration of the filtrate in vacuo
  6. customafforded a yellow oil
  7. customPurification of the crude product
  8. customthus obtained by way of flash chromatography (SiO2, 4:1 (v/v) Hex:EtOAc 3:7 (v/v) Hex:EtOAc)

출처 및 근거

ORD 기록
ord-dc0bbd6d8f4346c5a4e4e1198226eb3d
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889714B2

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