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

HRID 1911175Notes

Reaction equation

HRID 1911175 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-96b7e98c2a8f4c02bae9d8d51aca5e19
Source dataset
uspto-grants-2013_12
Patent number
US08604017B2

Reaction notes

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