反应 #163437

反应方程式

solution

N-[(5Z)-4-[(1Z)-but-1-enyl]-2-tert-butylisothiazol-5(2H)-ylidene]-5-chloro-2-methoxybenzamide

1,2-dimethoxyethane

diethylzinc

diiodomethane

→

title compound

收率 77.0%

N-[(5Z)-2-tert-butyl-4-(2-ethylcyclopropyl)isothiazol-5(2H)-ylidene]-5-chloro-2-methoxybenzamide

收率 77.0%

溶剂

CH2Cl2

反应条件

后处理

1. 1
   workup.ADDITIONAfter the addition
2. 2
   温度to warm to room temperature
3. 3
   workup.STIRRINGstir overnight
4. 4
   其他The reaction was quenched with NH4Cl
5. 5
   萃取acetone and extracted with EtOAc (2×)
6. 6
   干燥dried (MgSO4)
7. 7
   过滤filtered
8. 8
   其他solvent evaporated
9. 9
   其他The residue was purified by column chromatography

实验过程

To a solution of CH2Cl2 (10 mL) and 1,2-dimethoxyethane (95 mg, 1.06 mmol) at −10° C. was added diethylzinc (130 mg, 1.06 mmol). To this solution was added dropwise diiodomethane (565 mg, 2.1 mmol). After the addition was complete, the resulting clear solution was stirred for 10 min at −10° C. A solution of Example 25B (200 mg, 0.53 mmol) was added to the reaction mixture, which was allowed to warm to room temperature and stir overnight. The reaction was quenched with NH4Cl then acetone and extracted with EtOAc (2×). The organics were combined, dried (MgSO4), filtered and solvent evaporated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 159 mg (77%) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 0.59 (q, J=5.52 Hz, 1 H) 0.92 (t, J=7.36, 6.44 Hz, 3 H) 0.94-1.14 (m, 2 H) 1.16-1.29 (m, 2 H) 1.65 (s, 9 H) 2.11-2.33 (m, 1 H) 3.91 (s, 3 H) 6.91 (d, J=8.90 Hz, 1 H) 7.33 (dd, J=8.90, 2.76 Hz, 1 H) 7.81 (s, 1 H) 8.08 (d, J=2.76 Hz, 1 H); MS (DCI/NH4+) m/z 393 (M+H)+.

来源