反应 #164656

反应方程式

DEAD

Ph3P

(5-((3,4-dichlorophenyl)amino)pyrazin-2-yl)methanol

6-hydroxyquinolin-2(1H)-one

→

6-((5-(3,4-dichlorophenylamino)pyrazin-2-yl)methoxy)quinolin-2(1H)-one

收率 13.1%

溶剂

THF

THF

反应条件

后处理

1. 1
   workup.STIRRINGAfter stirring for 5 min
2. 2
   workup.STIRRINGThe reaction was stirred at room temperature overnight
3. 3
   浓缩The mixture was concentrated
4. 4
   其他partially purified by flash chromatography on silica gel using 30-100% ethyl acetate in hexanes
5. 5
   浓缩The desired fractions were concentrated to a solid, which
6. 6
   workup.DISSOLUTIONwas redissolved in DMF
7. 7
   workup.ADDITIONWater was added to the vigorously stirred solution until a suspension
8. 8
   其他formed
9. 9
   workup.STIRRINGAfter stirring 18 h
10. 10
    过滤the off-white solid was filtered
11. 11
    洗涤washed with methanol
12. 12
    其他dried

实验过程

A solution of Ph3P (0.07 g, 0.267 mmol) in THF (1.7 mL) was cooled to 0° C. under N2 and DEAD (0.076 ml, 0.481 mmol) was added dropwise. The mixture was stirred for 10 min, then 6-hydroxyquinolin-2(1H)-one (0.072 g, 0.444 mmol) was added. After stirring for 5 min, a solution of (5-((3,4-dichlorophenyl)amino)pyrazin-2-yl)methanol (0.1 g, 0.370 mmol) in THF (2 mL) was added. The reaction was stirred at room temperature overnight. The mixture was concentrated and partially purified by flash chromatography on silica gel using 30-100% ethyl acetate in hexanes, then 5-10% methanol in ethyl acetate. The desired fractions were concentrated to a solid, which was redissolved in DMF. Water was added to the vigorously stirred solution until a suspension formed. After stirring 18 h, the off-white solid was filtered, washed with methanol, and dried to yield 6-((5-(3,4-dichlorophenylamino)pyrazin-2-yl)methoxy)quinolin-2(1H)-one (0.02 g, 13%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.67 (1H, s), 9.97 (1H, s), 8.40 (1H, d, J=1.00 Hz), 8.28 (1H, d, J=1.51 Hz), 8.20 (1H, d, J=2.26 Hz), 7.86 (1H, d, J=9.79 Hz), 7.49-7.64 (2H, m), 7.37 (1H, s), 7.17-7.32 (2H, m), 6.51 (1H, dd, J=9.54, 2.01 Hz), 5.12 (2H, s). LCMS: R.T.=4.09; [M+H]+=412.93.

来源