Diethyl Ether → 1-methyl-3-(4-methylphenyl)-1H-indole

HRID 1868539Notes

Reaction equation

HRID 1868539 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH3:11])[CH:3]=1.CCO[CH2:15][CH3:16].[NH4+].[Cl-]>>[CH3:11][N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]([C:5]2[CH:10]=[CH:9][C:15]([CH3:16])=[CH:7][CH:6]=2)=[CH:3]1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 133577363-Bromo-1-methyl-1H-indole

Product 1

HCID 589315421-methyl-3-(4-methylphenyl)-1H-indole

Procedure

A mixture of 4.31 g (0.02 mol) of 3-bromo-1-methyl-1H-indole and 0.22 g (0.0004 mol) of NiCl2dppp was added to a solution of p-TolylMgBr in ether (prepared from 0.6 g of Mg (0.025 mol) and 4.21 g of TolylBr (0.024 mol) in 40 mL of ether) under stirring. The reaction mixture was stirred overnight. The resulting mixture was treated with 10% aqueous NH4Cl, the organic layer was separated, washed with 10% aqueous NH4Cl and then dried over anhydrous Na2SO4. The solution was evaporated to give an oil that crystallized. The product was washed with methanol and dried. Yield 2.2 g (49%) of colorless crystalline solid.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. customthe organic layer was separated
  3. washwashed with 10% aqueous NH4Cl
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solution was evaporated
  6. customto give an oil
  7. customthat crystallized
  8. washThe product was washed with methanol
  9. customdried

Sources & evidence

ORD record
ord-217f396e4bd643be86f89975759c2c32
Source dataset
uspto-grants-2009_12
Patent number
US07635781B2

Reaction notes

Loading…