Methyl iodide → 4-Bromo-1-methyl-1H-indole

HRID 1434572Notes

Reaction equation

HRID 1434572 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[H-].[Na+].I[CH3:14]>O1CCCC1>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[CH3:14]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 6764944-Bromoindole

Product 1

HCID 225589374-Bromo-1-methyl-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-bromo-1H-indole (6.7 g) in tetrahydrofuran (75 ml) was treated with sodium hydride (1.24 g) and stirred for 0.5 h at room temperature. The resulting suspension was treated with a solution of iodomethane (2.34 ml) in tetrahydrofuran (35 ml) at 0° C. and allowed to warm to room temperature over 1 h, whilst stirring. The reaction mixture was poured onto water and partitioned between dichloromethane and water. The organic phase was dried over (MgSO4) and concentrated in vacuo to afford the title compound (7.2 g). TLC Silica (cyclohexane-ethyl acetate [1:1]), Rf=0.55.

Workup

  1. temperatureto warm to room temperature over 1 h
  2. stirringwhilst stirring
  3. additionThe reaction mixture was poured onto water
  4. custompartitioned between dichloromethane and water
  5. dry with materialThe organic phase was dried over (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-14b71f2b526948998a1418bf2db31eab
Source dataset
uspto-grants-2009_11
Patent number
US07615550B2

Reaction notes

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