반응 #45409

반응 방정식

mixture

tert-butyl 4-(4-amino-7-iodothieno[3,2-c]pyridin-3-yl)phenylcarbamate

4-pyridylboronic acid

Na2CO3

→

desired product

수율 46.5%

tert-butyl 4-[4-amino-7-(4-pyridinyl)thieno[3,2-c]pyridin-3-yl]phenylcarbamate

수율 46.5%

용매

THF methanol water

반응 조건

후처리

1. 1
   기타by bubbling nitrogen through the solution for 15 minutes
2. 2
   기타The reaction vessel was sealed
3. 3
   온도The reaction was cooled to room temperature
4. 4
   기타partitioned between water and ethyl acetate
5. 5
   추출The aqueous phase was extracted twice with ethyl acetate
6. 6
   건조The combined extracts were dried (Na2SO4)
7. 7
   여과filtered
8. 8
   농축concentrated
9. 9
   기타the residue was purified by flash column chromatography on silica gel with 3% methanol/dichloromethane

실험 절차

A mixture of Example 77A (1.559 g, 3.34 mmol), 4-pyridylboronic acid (0.431 g, 3.51 mmol) and Na2CO3 (0.37 g, 3.51 mmol) in THF/methanol/water (12 mL:2.4 mL:4 mL) was degassed by bubbling nitrogen through the solution for 15 minutes, then treated with Pd(dppf)Cl2 (136mg, 0.17 mmol). The reaction vessel was sealed and heated to 90° C. for 17 hours. The reaction was cooled to room temperature and partitioned between water and ethyl acetate. The aqueous phase was extracted twice with ethyl acetate. The combined extracts were dried (Na2SO4), filtered, concentrated, and the residue was purified by flash column chromatography on silica gel with 3% methanol/dichloromethane to provide 0.65 g (46%) of the desired product. MS (ESI(+)) m/e 419 (M+H)+.

출처