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

Participants

Reaction Steps

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.

Provenance & Evidence