Triacetoxyperiodinane → 2-(3-bromo-quinolin-6-yloxy)-N-(1,1-dimethyl-2-oxo-ethyl)-2-methylsulfanyl-acetamide

HRID 1892040Notes

Reaction equation

HRID 1892040 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:22][CH3:23])[C:14]([NH:16][C:17]([CH3:21])([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:22][CH3:23])[C:14]([NH:16][C:17]([CH3:20])([CH3:21])[CH:18]=[O:19])=[O:15])=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 667178702-(3-bromo-quinolin-6-yloxy)-N-(2-hydroxy-1,1-dimethyl-ethyl)-2-methylsulfanyl-acetamide

Product 1

HCID 866480202-(3-bromo-quinolin-6-yloxy)-N-(1,1-dimethyl-2-oxo-ethyl)-2-methylsulfanyl-acetamideYield 94.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3-Bromo-quinolin-6-yloxy)-N-(2-hydroxy-1,1-dimethyl-ethyl)-2-methylsulfanyl-acetamide (0.2 g) from Stage 2, Step 1 above in dichloromethane (15 ml) was treated with Dess-Martin periodinane (0.42 g). The reaction mixture was stirred at rt for 1 hour. 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 magnesium sulphate, filtered and evaporated. The residue was purified by column chromatography (heptane/ethyl acetate 1:1) to give 2-(3-bromo-quinolin-6-yloxy)-N-(1,1-dimethyl-2-oxo-ethyl)-2-methylsulfanyl-acetamide as white solid (0.188 g). 1H NMR (CDCl3) δ ppm: 9.41 (1H, s); 8.83 (1H, d); 8.26 (1H, d); 8.08 (1H, d); 7.51 (1H, dd); 7.22 (1H, d); 5.69 (1H, s); 2.20 (3H, s); 1.53 (6H, s).

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 magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography (heptane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-a2a9304921e04a3882deeba7354587f0
Source dataset
uspto-grants-2013_08
Patent number
US08507509B2

Reaction notes

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