Dimethylformamide → HCID 21714274, compound

HRID 1600624Notes

Reaction equation

HRID 1600624 reaction equation
[CH3:1][N:2]([C:10]1[CH:11]=[CH:12][C:13]([C:24]([F:27])([F:26])[F:25])=[C:14]2[C:18]=1[NH:17][C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:15]2)[CH2:3][CH2:4]OS(C)(=O)=O.[H-].[Na+].CN(C)C=O>O>[CH3:1][N:2]1[C:10]2[CH:11]=[CH:12][C:13]([C:24]([F:25])([F:26])[F:27])=[C:14]3[CH:15]=[C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:17]([C:18]=23)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 21714327HCID 21714327, compound

Product 1

HCID 21714274HCID 21714274, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 7-[N-methyl-N-(2-methanesulfonyloxyethyl)amino]-4-trifluoromethyl-1H-indole-2-carboxylate (3.15 g, 7.71 mmol), 60% sodium hydride (0.31 g, 7.71 mmol) and N,N-dimethylformamide (200 ml) was stirred at room temperature for 1 hour. The reaction mixture was poured into cold water and extracted with ethyl acetate, and the extract solution was washed with a 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was recrystallized from isopropanol to obtain ethyl 2,3-dihydro-1-methyl-7-trifluoromethyl-1H-pyrrolo[1,2,3-de]quinoxaline-5-carboxylate. M.p. 91-92° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe extract solution was washed with a 5% aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-5ace70f10e984d99bf745ba486108266
Source dataset
uspto-grants-1999_11
Patent number
US05977100

Reaction notes

Loading…