Sodium borohydride → HCID 59238256, compound

HRID 1359915Notes

Reaction equation

HRID 1359915 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([NH:12][C:13](=[O:15])[CH3:14])=[C:6]([C:16](=O)[C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH3:24])=[CH:19][CH:18]=2)[CH:5]=1>C(O)C>[Br:3][C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([NH:12][C:13](=[O:15])[CH3:14])=[C:6]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH3:24])=[CH:21][CH:22]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59238224HCID 59238224, compound

Product 1

HCID 59238256HCID 59238256, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.17 g) is added portionwise to an ice-cold suspension of N-[4-bromo-2-(4-ethyl-benzoyl)-5-methoxy-phenyl]-acetamide (3.25 g) in ethanol (50 mL). The cooling bath is removed and the solution is stirred at ambient temperature for 2 h. Then, 1 M aqueous NaOH solution (8.5 mL) is added and the resulting solution is concentrated under reduced pressure. Water is added to the residue and the resulting mixture is extracted with ethyl acetate. The combined organic extracts are washed with brine, dried (Na2SO4) and concentrated. The residue is taken up in trifluoroacetic acid (20 mL) and triethylsilane (4.3 mL) is added. The solution is stirred at ambient temperature overnight and then poured on crushed ice. The resultant mixture is extracted twice with ethyl acetate. The combined extracts are washed with brine, dried (sodium sulphate) and concentrated under reduced pressure. The residue is treated with methanol and the precipitate formed is separated. The precipitate is then washed with diisopropylether and dried to give the desired product.

Workup

  1. customThe cooling bath is removed
  2. additionThen, 1 M aqueous NaOH solution (8.5 mL) is added
  3. concentrationthe resulting solution is concentrated under reduced pressure
  4. additionWater is added to the residue
  5. extractionthe resulting mixture is extracted with ethyl acetate
  6. washThe combined organic extracts are washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. additiontriethylsilane (4.3 mL) is added
  10. stirringThe solution is stirred at ambient temperature overnight
  11. additionpoured
  12. customon crushed ice
  13. extractionThe resultant mixture is extracted twice with ethyl acetate
  14. washThe combined extracts are washed with brine
  15. dry with materialdried (sodium sulphate)
  16. concentrationconcentrated under reduced pressure
  17. additionThe residue is treated with methanol
  18. customthe precipitate formed
  19. customis separated
  20. washThe precipitate is then washed with diisopropylether
  21. customdried

Sources & evidence

ORD record
ord-8e9b98a5295a4c9c9f513ad34bfaab94
Source dataset
uspto-grants-2011_02
Patent number
US07879806B2

Reaction notes

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