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

참여 물질

반응 단계

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).

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