Methyl iodide → 3-(2-chloropyrimidin-4-yl)-1-methyl-1H-indole

HRID 1947007Notes

Reaction equation

HRID 1947007 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:9]=[C:8]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)[CH:7]=[CH:6][N:5]=1.I[CH3:20]>CN(C=O)C>[Cl:3][C:4]1[N:9]=[C:8]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH3:20])[CH:11]=2)[CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 597434283-(2-Chloropyrimidin-4-yl)-1H-indole

Product 1

HCID 597435953-(2-chloropyrimidin-4-yl)-1-methyl-1H-indoleYield 110.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60% dispersion in mineral oil, 0.16 g, 7 mmol) was added at 0° C. to 3-(2-chloro-pyrimidin-4-yl)-1H-indole (0.24 g, 1 mmol) in DMF (8 mL). The resulting mixture was stirred for 10 min, then iodomethane (0.20 mL, 3.2 mmol) was added, and the reaction mixture was warmed to RT and poured onto ice water. The resulting mixture was extracted with EtOAc, the combined organics washed twice with water, dried over Na2SO4, filtered and concentrated under reduced pressure to give 3-(2-chloro-pyrimidin-4-yl)-1-methyl-1H-indole (270 mg) as a yellow solid.

Workup

  1. additionpoured onto ice water
  2. extractionThe resulting mixture was extracted with EtOAc
  3. washthe combined organics washed twice with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c5e4a1b72e514b519199e456393d8e68
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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