Ammonium Chloride → HCID 20708402, compound

HRID 430800Notes

Reaction equation

HRID 430800 reaction equation
CC(C)([O-])C.[K+].Br[CH2:8][C:9]([O:11][CH3:12])=[O:10].[C:13]1([CH:19]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:20][CH2:21][CH2:22][N:23]2[C:31]3[C:26](=[C:27]([OH:32])[CH:28]=[CH:29][CH:30]=3)[CH2:25][CH2:24]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[NH4+]>CN(C=O)C>[C:33]1([CH:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:20][CH2:21][CH2:22][N:23]2[C:31]3[C:26](=[C:27]([O:32][CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:28]=[CH:29][CH:30]=3)[CH2:25][CH2:24]2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 60984Methyl bromoacetateHCID 18351715HCID 18351715, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20708402HCID 20708402, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under argon atmosphere, potassium t-butoxide (586 mg) and methyl bromoacetate (2.50 ml) were added to 1-(2-(diphenylmethoxy)ethyl)-4-hydroxyindoline (855 mg) in DMF (15 ml), and the obtained mixture was stirred at room temperature for 2 hours. To the reaction mixture, saturated aqueous ammonium chloride solution (5 ml) was added to stop the reaction and the resultant was extracted with ethyl acetate. The obtained organic layer was washed and dried over sodium sulfate. After removing solids by filtration, the solvent was removed under reduced pressure and the obtained crude product was purified by silica gel column chromatography to obtain the desired compound (571 mg, yield: 55%)

Workup

  1. customthe reaction
  2. extractionthe resultant was extracted with ethyl acetate
  3. washThe obtained organic layer was washed
  4. dry with materialdried over sodium sulfate
  5. customAfter removing solids
  6. filtrationby filtration
  7. customthe solvent was removed under reduced pressure
  8. customthe obtained crude product
  9. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-36ca81bc4920496e8ddbfcbabada41d4
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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