Reaktion #2329008

Reaktionsgleichung

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

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred at room temperature overnight
2. 2
   SonstigeThe reaction mixture was then partitioned between EtOAc (100 mL) and water (250 mL)
3. 3
   Extraktionthe aqueous layer was extracted twice with EtOAc (100 mL)
4. 4
   WaschenThe combined organic layers were washed with brine (100 mL)
5. 5
   Trocknendried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated

Vorschrift

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).

Quelle