1-Bromo-3-methylbutane → 4-[1-(3-Methyl-butyl)-6-nitro-1H-indol-3-yl]-benzonitrile

HRID 2079896

반응식

HRID 2079896 반응식
C([O-])([O-])=O.[Cs+].[Cs+].[N+:7]([C:10]1[CH:18]=[C:17]2[C:13]([C:14]([C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=3)=[CH:15][NH:16]2)=[CH:12][CH:11]=1)([O-:9])=[O:8].[CH2:27](Br)[CH2:28][CH:29]([CH3:31])[CH3:30]>CN(C=O)C>[CH3:30][CH:29]([CH3:31])[CH2:28][CH2:27][N:16]1[C:17]2[C:13](=[CH:12][CH:11]=[C:10]([N+:7]([O-:9])=[O:8])[CH:18]=2)[C:14]([C:19]2[CH:20]=[CH:21][C:22]([C:23]#[N:24])=[CH:25][CH:26]=2)=[CH:15]1

참가 물질

5

반응물 3

HCID 78911-Bromo-3-methylbutaneHCID 10796Cesium carbonateHCID 574421974-(6-nitro-1H-indol-3-yl)-benzonitrile

생성물 1

HCID 574421904-[1-(3-Methyl-butyl)-6-nitro-1H-indol-3-yl]-benzonitrile수율 95%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Method L Add Cs2CO3 (1.0 g, 1.88 mmol) to a solution of 4-(6-Nitro-1H-indol-3-yl)-benzonitrile, 9, (100 mg, 0.37 mmol) and isopentyl bromide (0.1 mL, 0.75 mmol) in DMF (10 mL). Stir overnight at ambient temperature. Remove the DMF solvent to provide a solid and partition the solid between EtOAc and H2O, Sequentially wash the organic layer with H2O and brine then dry the organic layer over MgSO4. Filter and remove the solvent leaving a solid. Purify by silica gel column chromatography (0-100% EtOAc/hexanes gradient) and concentrated to dryness to afford 180 mg (95%) of the title compound. LRMS (API ES+)=334.3 (M+H).

후처리

  1. customRemove the DMF solvent
  2. customto provide a solid
  3. custompartition the solid between EtOAc and H2O
  4. washSequentially wash the organic layer with H2O and brine
  5. dry with materialthen dry the organic layer over MgSO4
  6. filtrationFilter
  7. customremove the solvent
  8. customleaving a solid
  9. customPurify by silica gel column chromatography (0-100% EtOAc/hexanes gradient)
  10. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-55ac11c51faa4283ae924097c48e9388
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932284B2

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