Iodoethane → HCID 90449559, compound

HRID 1411266Notes

Reaction equation

HRID 1411266 reaction equation
[C:1]([N:4]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=3)[N:10]([C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH2:9]2)[CH2:5]1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:31][CH3:32].C(OCC)(=O)C>CN(C)C=O>[C:1]([N:4]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:31][CH3:32])[CH:15]=3)[N:10]([C:18](=[O:23])[C:19]([F:21])([F:22])[F:20])[CH2:9]2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 90449646HCID 90449646, compound

Product 1

HCID 90449559HCID 90449559, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 1-(1′-acetyl-5-hydroxyspiro[indoline-3,3′-pyrrolidin]-1-yl)-2,2,2-trifluoroethanone (40 mg, 0.122 mmol) obtained in Step 2 of Example 198 was dissolved in N,N-dimethylformamide (0.5 mL). Thereafter, cesium carbonate (52 mg, 0.159 mmol) and iodoethane (23 mg, 0.146 mmol) were added to the above obtained solution, and the thus obtained mixture was then stirred at room temperature for 18 hours. Thereafter, ethyl acetate was added to the reaction solution, and the reaction mixture was then washed with water and brine. The resultant was dried over anhydrous sodium sulfate. The solvent was distilled away, and the obtained residue was then purified by silica gel column chromatography (ethyl acetate) to obtain 1-(1′-acetyl-5-ethoxyspiro[indoline-3,3′-pyrrolidin]-1-yl)-2,2,2-trifluoroethanone (24 mg, 54%) in the form of a colorless oily product.

Workup

  1. washthe reaction mixture was then washed with water and brine
  2. dry with materialThe resultant was dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled away
  4. customthe obtained residue was then purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-af0260889686496c857b3874013e2c73
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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