Methyl iodide → 3-(2-Bromoethyl)-1-methyl-1H-indole

HRID 624051Notes

Reaction equation

HRID 624051 reaction equation
[H-].[Na+].[CH3:3]I.[Br:5][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1>C1COCC1>[Br:5][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH3:3])[CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 769243-(2-Bromoethyl)indole

Product 1

HCID 131533063-(2-Bromoethyl)-1-methyl-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A flask was charged with NaH (900 mg, 37.52 mmol), MeI (3.14 mL, 50.00 mmol) and THF (7.5 mL). The resulting grey suspension was stirred at rt for 5 min, then a solution of 3-(2-bromethyl)-indol (1.12 g, 5.00 mmol) in THF (25 mL) was added dropwise. After stirring for 18 h at rt, the reaction mixture was concentrated, redissolved in DCM and washed with H2O (3×). The org. layer was dried (MgSO4), filtered and the solvent was removed under reduced pressure to yield the title compound as an yellow oil which was used as such in the next step. LC-MS conditions A: tR=0.95 min, [M+H]+=no ionization.

Workup

  1. stirringAfter stirring for 18 h at rt
  2. concentrationthe reaction mixture was concentrated
  3. dissolutionredissolved in DCM
  4. washwashed with H2O (3×)
  5. dry with materiallayer was dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-798d6f26c67040a19d0eab326fdd523e
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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