Dimethylformamide → HCID 66751174, compound

HRID 534892Notes

Reaction equation

HRID 534892 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([N:20]1[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:22][CH2:21]1)=[O:19])=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.IC.[H-].[Na+].[CH3:40]N(C)C=O>O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:40])[C:13]([C:18]([N:20]1[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:22][CH2:21]1)=[O:19])=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66792775HCID 66792775, compound

Product 1

HCID 66751174HCID 66751174, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-(benzyloxy)-2-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}-1H-indole obtained in Example 23 (880 mg), iodomethane (0.143 mL), sodium hydride (92 mg, 60% in oil dispersion), and N,N-dimethylformamide (5 mL) was stirred at room temperature for 16 h. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to provide the title compound (860 mg, 95%) as crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-063e60f141504bb89134b4e4770b15ac
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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