Methyl iodide → Methyl 3-(4-fluorophenyl)-1-methyl-1H-indole-6-carboxylate

HRID 2365663Notes

Reaction equation

HRID 2365663 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:15]=3)[NH:10][CH:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:23]I>CN(C=O)C.CCOC(C)=O.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:14][CH:15]=3)[N:10]([CH3:23])[CH:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59625721methyl 3-(4-fluorophenyl)-1H-indole-6-carboxylate

Product 1

HCID 59625676Methyl 3-(4-fluorophenyl)-1-methyl-1H-indole-6-carboxylateYield 119.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound 53d (300 mg, 0.78 mmol) in DMF (3 mL) was added NaH (60% in mineral oil, 68.9 mg, 1.72 mmol) at 0° C. The mixture was stirred at 0° C. for 30 min, then CH3I (0.053 mL, 0.86 mmol) was added and stirring continued at 0° C. for another 1 h. The resulting mixture was diluted with EtOAc and water. The organic layer was washed with brine and concentrated. The residue was recrystallized from heptane, filtered and dried the solid to give compound 53f (265 mg) as a light yellow solid. MS m/z (M+H+) 284.1.

Workup

  1. stirringstirring
  2. waitcontinued at 0° C. for another 1 h
  3. washThe organic layer was washed with brine
  4. concentrationconcentrated
  5. customThe residue was recrystallized from heptane
  6. filtrationfiltered
  7. customdried the solid

Sources & evidence

ORD record
ord-a45eb0b2fce749d89f2c0727a7cc8734
Source dataset
uspto-grants-2014_04
Patent number
US08697683B2

Reaction notes

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