Methyl iodide → 3-(2-Bromoethyl)-5-methoxy-1-methyl-1H-indole

HRID 624049Notes

Reaction equation

HRID 624049 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]=[C:14]([O:17][CH3:18])[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]=[C:14]([O:17][CH3:18])[CH:15]=2)[N:10]([CH3:3])[CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 111078683-(2-bromoethyl)-5-methoxy-1H-indole

Product 1

HCID 214599183-(2-Bromoethyl)-5-methoxy-1-methyl-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A flask was charged with NaH (145 mg, 3.62 mmol), MeI (0.45 mL, 7.24 mmol) and THF (1.7 mL). The resulting grey suspension was stirred at rt for 5 min, then a solution of 3-(2-bromo-ethyl)-5-methoxy-1H-indole (230 mg, 0.90 mmol) in THF (4.1 mL) was added dropwise. After stirring for 18 h at rt, the reaction mixture was concentrated and purification by FC (hex/EtOAc 2:1, Rf=0.5) yielded the title compound as an yellow solid. LC-MS conditions 08Z acidic tR=0.93 min, [M+H]+=no ionization.

Workup

  1. stirringAfter stirring for 18 h at rt
  2. concentrationthe reaction mixture was concentrated
  3. custompurification by FC (hex/EtOAc 2:1, Rf=0.5)

Sources & evidence

ORD record
ord-c8d1366058ab4af2b1e0f2bcfb9e2e0d
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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