Dimethylformamide → 1-cyclopropylmethyl-6-ethoxy-2-(4-nitro-phenyl)-1H-indole

HRID 502270Notes

Reaction equation

HRID 502270 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[C:9]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=3)[NH:10]2)=[CH:6][CH:5]=1)[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C.Br[CH2:34][CH:35]1[CH2:37][CH2:36]1>O>[CH:35]1([CH2:34][N:10]2[C:11]3[C:7](=[CH:6][CH:5]=[C:4]([O:3][CH2:1][CH3:2])[CH:12]=3)[CH:8]=[C:9]2[C:13]2[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=2)[CH2:37][CH2:36]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 590304256-ethoxy-2-(4-nitro-phenyl)-1H-indole

Product 1

HCID 590304261-cyclopropylmethyl-6-ethoxy-2-(4-nitro-phenyl)-1H-indoleYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-Ethoxy-2-(4-nitro-phenyl)-1H-indole (4.5 g, 16 mmol), Cs2CO3 (7.8 g, 24 mmol), DMF (23 mL), and bromomethylcyclopropane (1.8 mL, 18 mmol) were stirred at 80° C. in a sealed tube for 16 hours. The reaction mixture was diluted with H2O and extracted with EtOAc. The organic layer was washed with H2O and brine and then dried and concentrated. Purification by silica gel chromatography (1:1 CH2Cl2/hexane) provided 1-cyclopropylmethyl-6-ethoxy-2-(4-nitro-phenyl)-1H-indole (4.73 g, 88%) as an orange solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with H2O and brine
  3. customdried
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (1:1 CH2Cl2/hexane)

Sources & evidence

ORD record
ord-30a61c31ea61401787f5f6a3dc3872f8
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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