HRID1054882

反应详情

EQUATION

反应方程式

HRID 1054882 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

3

CONDITIONS

反应条件

温度
0 °C

PROCEDURE

实验过程

To a solution of 4,6-difluoro-5-{4-[1-(hydroxymethyl)cyclobutyl]phenyl}-1H-indole-3-carbaldehyde (34 mg, 0.10 mmol) in acetonitrile (5 mL) and tert butanol (5 mL) was added 2-methyl-2-butene (700 g, 10.0 mmol). The mixture was cooled to 0° C. with ice bath. The sodium chlorite (273 mg, 3.00 mmol) and sodium dihydrogenphosphate (360 mg, 3.00 mmol) were dissolved in water (5 mL). The aqueous was added to the organic solution and the mixture was allowed to warm to room temperature. The reaction mixture was stirred at room temperature for 48 hours. TLC (petroleum ether/ethyl acetate=1:1) showed the reaction was complete. A solution of sodium sulfite was added slowly to the stirring mixture. The reaction mixture was allowed to stir 1 hour. Then the organics were removed under reduced pressure. The aqueous layer was extracted with ethyl acetate (20 mL×3). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to give a brown residue. The residue was purified by preparative reverse phase HPLC to give the title compound (15 mg, 42%) as a white solid. MS (ES+) 380.0 (M+Na)+. 1H NMR (400 MHz, CD3OD) δ 8.01 (s, 1H), 7.41 (d, 1H), 7.28 (d, 2H), 7.14 (d, 2H), 3.76 (s, 2H), 2.36 (m, 4H), 2.13 (m, 1H), 1.93 (m, 1H).

WORKUP

后处理

  1. additionThe aqueous was added to the organic solution
  2. temperatureto warm to room temperature
  3. stirringto stir 1 hour
  4. customThen the organics were removed under reduced pressure
  5. extractionThe aqueous layer was extracted with ethyl acetate (20 mL×3)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a brown residue
  10. customThe residue was purified by preparative reverse phase HPLC