Methyl iodide → 3-(2-Bromoethyl)-6-methoxy-1-methyl-1H-indole

HRID 624053Notes

Reaction equation

HRID 624053 reaction equation
[H-].[Na+].[CH3:3]I.[Br:5][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[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][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[N:10]([CH3:3])[CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 117368993-(2-bromoethyl)-6-methoxy-1H-indole

Product 1

HCID 867042163-(2-Bromoethyl)-6-methoxy-1-methyl-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A flask was charged with NaH (110 mg, 4.60 mmol), MeI (0.39 mL, 6.13 mmol) and THF (1.5 mL). The resulting grey suspension was stirred at rt for 5 min, then a solution of 3-(2-Bromo-ethyl)-6-methoxy-1H-indole (156 mg, 0.61 mmol) in THF (2.5 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 B: tR=0.94 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-258314b0a4df45cf9def54f8ae41cafa
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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