反应详情

Bestmann's reagent ((1-diazo-2-oxo-propyl)-phosphonic acid dimethyl ester) (123 mg) was added to a solution of 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-formyl-cyclobutyl)-2-methylsulfanyl-acetamide (180 mg) from Step 2 above in MeOH (15 ml) under nitrogen atmosphere. After cooling to 0° C. potassium carbonate (114 mg) was added and the mixture was stirred overnight at temperature from 0° C. to room temperature, then poured into brine and extracted with ethyl acetate (2×). The combined organic layers were washed with water, dried over sodium sulphate anhydrous, filtered and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate/CH2Cl2, 1/1/3) to give N-(1-ethynyl-cyclobutyl)-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide (106 mg) as white solid.

1. additionwas added
2. extractionextracted with ethyl acetate (2×)
3. washThe combined organic layers were washed with water
4. dry with materialdried over sodium sulphate anhydrous
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe crude residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate/CH2Cl2, 1/1/3)