2-Bromopropane → 1H-Indole,4-bromo-1-(1-methylethyl)-6-(trifluoromethyl)-

HRID 873367Notes

Reaction equation

HRID 873367 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[H-].[Na+].Br[CH:18]([CH3:20])[CH3:19]>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[CH:18]([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 247292314-Bromo-6-(trifluoromethyl)-1H-indole

Product 1

HCID 674685331H-Indole,4-bromo-1-(1-methylethyl)-6-(trifluoromethyl)-Yield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-6-(trifluoromethyl)-1H-indole (1 g, 3.79 mmol) in DMF (6 mL) was added 60% sodium hydride (0.182 g, 4.54 mmol), and the mixture was stirred for 30 min. 2-bromopropane (0.533 mL, 5.68 mmol) was added and the mixture was stirred overnight. The reaction was then quenched with 10% NaHCO3 and extracted with EtOAc (3×). The extract was dried over Na2SO4 and concentrated. The residue was purified using column chromatography (Silica gel, 0 to 100% EtOAc/hexanes) to give the title compound (460 mg, 40%) as white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.56-1.61 (m, 6 H), 4.66-4.79 (m, 1 H), 6.65 (d, J=3.03 Hz, 1 H), 7.27-7.31 (m, 1 H), 7.45 (d, J=3.03 Hz, 1 H), 7.54 (s, 1 H), 7.63 (s, 1 H). MS: (M+H)+=306.2.

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe reaction was then quenched with 10% NaHCO3
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe extract was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-1c1763ef2a7f4eb580dfb4d38b69dbe2
Source dataset
uspto-grants-2015_03
Patent number
US08975291B2

Reaction notes

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