反应 #2329008

反应方程式

2-(6-aminopyridin-3-yl)-1,3-benzoxazol-6-ol

tert-butylchlorodimethylsilane

imidazole

tert-butylchlorodimethylsilane

imidazole

→

yellow solid

5-(6-{[tert-butyl(dimethyl)silyl]oxy}-1,3-benzoxazol-2-yl)pyridin-2-amine

溶剂

DMF

反应条件

后处理

1. 1
   workup.STIRRINGstirred at room temperature overnight
2. 2
   其他The reaction mixture was then partitioned between EtOAc (100 mL) and water (250 mL)
3. 3
   萃取the aqueous layer was extracted twice with EtOAc (100 mL)
4. 4
   洗涤The combined organic layers were washed with brine (100 mL)
5. 5
   干燥dried (Na2SO4)
6. 6
   过滤filtered
7. 7
   其他evaporated

实验过程

To a solution of 2-(6-aminopyridin-3-yl)-1,3-benzoxazol-6-ol (0.95 mmol) in DMF (25 mL) was added tert-butylchlorodimethylsilane (1.05 mmol) and imidazole (2.38 mmol), the resulting mixture was stirred at room temperature for 3 hours. LCMS showed no conversion. Additional tert-butylchlorodimethylsilane (1.05 mmol) and imidazole (2.38 mmol) was added to the reaction mixture, then stirred at room temperature overnight. The reaction mixture was then partitioned between EtOAc (100 mL) and water (250 mL), and the aqueous layer was extracted twice with EtOAc (100 mL). The combined organic layers were washed with brine (100 mL), dried (Na2SO4), filtered and evaporated to give 1.121 g of a yellow solid. Purified by flash column chromatography (SiO2, Heptane:EtOAc 0→100%), to give the title compound (322.5 mg) as an ivory-white solid. 1H NMR δ ppm 8.67 (d, 1H) 8.01 (dd, 1H) 7.54 (d, 1H) 7.18 (d, 1H) 6.85 (dd, 1H) 6.77 (s, 2H) 6.57 (d, 1H) 0.97 (s, 9H) 0.22 (s, 6H); MS m/z 342 (M+H).

来源