Triacetoxyperiodinane → 2-(3-Bromo-quinolin-6-yloxy)-N-(1-cyano-1-methyl-2-oxo-ethyl)-2-methylsulfanyl-acetamide

HRID 1892045Notes

Reaction equation

HRID 1892045 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH:13]([S:23][CH3:24])[C:14]([NH:16][C:17]([C:21]#[N:22])([CH3:20])[CH2:18][OH:19])=[O:15])=[CH:7][CH:6]=2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH:13]([S:23][CH3:24])[C:14]([NH:16][C:17]([C:21]#[N:22])([CH3:20])[CH:18]=[O:19])=[O:15])=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 667174052-(3-Bromo-quinolin-6-yloxy)-N-(1-cyano-2-hydroxy-1-methyl-ethyl)-2-methylsulfanyl acetamide

Product 1

HCID 866480222-(3-Bromo-quinolin-6-yloxy)-N-(1-cyano-1-methyl-2-oxo-ethyl)-2-methylsulfanyl-acetamideYield 60.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3-Bromo-quinolin-6-yloxy)-N-(1-cyano-2-hydroxy-1-methyl-ethyl)-2-methylsulfanyl acetamide (0.660 g) from Stage 1 above in dichloromethane (25 ml) was treated with Dess-Martin periodinane (0.819 g). The reaction mixture was stirred at R.T. for 2 h 30. The reaction mixture was quenched with sat. aqueous NaHCO3 and sat. aqueous sodium thiosulphate. The reaction mixture was vigorously stirred at rt. for 30 minutes after which time the two phases were separated. The organic layer was washed with sat. aqueous. NaHCO3. After separation the organic phase was dried over sodium sulphate, filtered and evaporated to yield 0.397 g of 2-(3-Bromo-quinolin-6-yloxy)-N-(1-cyano-1-methyl-2-oxo-ethyl)-2-methylsulfanyl-acetamide as a crude product which was used in the next step without any further purification.

Workup

  1. customThe reaction mixture was quenched with sat. aqueous NaHCO3 and sat. aqueous sodium thiosulphate
  2. stirringThe reaction mixture was vigorously stirred at rt
  3. customfor 30 minutes after which time the two phases were separated
  4. washThe organic layer was washed with sat. aqueous
  5. customAfter separation the organic phase
  6. dry with materialwas dried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-9838cc6573304717b6078f38237e6ea5
Source dataset
uspto-grants-2013_08
Patent number
US08507509B2

Reaction notes

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