HRID338440

反应详情

EQUATION

反应方程式

HRID 338440 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

2

CONDITIONS

反应条件

温度
0 °C

PROCEDURE

实验过程

To a mixture of 6-chloro-5-[4-(oxetan-3-ylmethoxy)phenyl]-1H-indole-3-carbaldehyde (70 mg, 0.2 mmol) in acetonitrile/t-butanol=1/1(5 mL) was added 2-methyl-2-butene (0.5 mL). The reaction was cooled to 0° C. and an aqueous solution of sodium chlorite (180 mg, 2.00 mmol) and sodium dihydrogen phosphate (270 mg, 6.00 mmol) in water (0.5 mL) were added dropwise via additional funnel. Then ice bath was removed, the reaction was stirred at room temperature for 12 h. The reaction was quenched with sodium sulfite. The mixture was partitioned between EtOAc (20 mL×3) and water. The combined organics was concentrated to give a residue, which was purified by reverse phase HPLC to give the title compound (25 mg, 35% yield) as an off-white solid. MS (AP+) 358.1 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 8.04 (s, 1H), 7.95 (s, 1H), 7.61 (s, 1H), 7.35 (d, 2H), 7.04 (d, 2H), 4.74 (t, 2H), 4.46 (t, 2H), 4.26 (t, 2H), 3.44-3.42 (m, 1H).

WORKUP

后处理

  1. customThen ice bath was removed
  2. customThe reaction was quenched with sodium sulfite
  3. customThe mixture was partitioned between EtOAc (20 mL×3) and water
  4. concentrationThe combined organics was concentrated
  5. customto give a residue, which
  6. customwas purified by reverse phase HPLC