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

HRID 2079896

Reaction equation

HRID 2079896 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-55ac11c51faa4283ae924097c48e9388
Source dataset
uspto-grants-2011_04
Patent number
US07932284B2

Linked notes

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