Methyl iodide → 7-Bromo-1-methyl-1H-indole

HRID 2215752Notes

Reaction equation

HRID 2215752 reaction equation
[H-].[Na+].CI.[Br:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][CH:12]=[CH:11]2.[C:15]([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O>[CH3:15][N:13]1[C:14]2[C:10](=[CH:9][CH:8]=[CH:7][C:6]=2[Br:5])[CH:11]=[CH:12]1

Participants

7

Reactant 4

HCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 27570207-Bromoindole

Product 1

HCID 219500697-Bromo-1-methyl-1H-indole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A 60% dispersion of sodium hydride in mineral oil (1.40 g, 97 mmol) was washed with hexanes (3×10 mL, 1×5 mL), suspended in THF (50 mL) and CH3I added (1.64 mL, 26.3 mmol) followed by a solution of 7-bromoindole (4.06 g, 20.7 mmol) in THF (15 mL), with vigorous gas evolution. After 1 h at rt, the mixture was treated with additional CH3I (0.28 mL, 4.5 mmol) and stirred overnight. Saturated aq NaHCO3 was added and the mixture poured into EtOAc, which was separated, washed with saturated aq NaHCO3, dried (MgSO4) and concentrated to afford 1-methyl-7-bromoindole as an off-white semisolid which was used without further purification.

Workup

  1. customwas separated
  2. washwashed with saturated aq NaHCO3
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-77eeff928b9342fe89df7a6ccbcc8bbb
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

Loading…