反应详情

Sodium hydroxide (5.5 mL, 0.5 M in EtOH) was added to a mixture of 6-[5-(5-chloro-6-isopropoxy-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-1H-indole-3-carbaldehyde (D102) (200 mg) and piperidine-4-carboxylic acid ethyl ester hydrochloride (507 mg). The reaction mixture was stirred at room temperature for 10 mins, and AcOH (0.5 ml) was added. After the solvent was evaporated, the residue was dissolved in DCM (40 mL). NaBH(OAc)3 (554 mg) was then added in one portion. After stirred overnight, the reaction was quenched with saturated aqueous sodium bicarbonate solution, and extracted with DCM for 3 times. The combined organic solution was washed with brine, and dried over anhydrous sodium sulfate. The dried solution was concentrated. The residue was purified by Mass Directed AutoPrep to afford ethyl 1-{[6-(5-{5-chloro-6-[(1-methylethyl)oxy]-3-pyridinyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]methyl}-4-piperidinecarboxylate (D103) (140 mg) as a white solid. MS (ES): C27H30ClN5O4 requires 523; found 524.2.

1. customAfter the solvent was evaporated
2. dissolutionthe residue was dissolved in DCM (40 mL)
3. additionNaBH(OAc)3 (554 mg) was then added in one portion
4. stirringAfter stirred overnight
5. customthe reaction was quenched with saturated aqueous sodium bicarbonate solution
6. extractionextracted with DCM for 3 times
7. washThe combined organic solution was washed with brine
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationThe dried solution was concentrated
10. customThe residue was purified by Mass Directed AutoPrep