반응 #534199

반응 방정식

1-(7-Bromo-5-pyridin-3-yl-benzothiazol-2-yl)-3-ethyl-urea

2-fluorobenzeneboronic acid

potassium phosphate tribasic

→

pale-brown solid

수율 23.0%

1-Ethyl-3-[7-(2-fluoro-phenyl)-5-pyridin-3-yl-benzothiazol-2-yl]-urea

수율 23.0%

용매

1,4-dioxane

methanol

반응 조건

후처리

1. 1
   기타was purged with nitrogen for 5 min
2. 2
   온도After cooling to ambient temperature
3. 3
   여과the mixture was filtered through kieselguhr
4. 4
   세척The kieselguhr was thoroughly washed with methanol
5. 5
   기타the combined filtrates evaporated to dryness in vacuo
6. 6
   기타to give the crude 1-Ethyl-3-[7-(2-fluoro-phenyl)-5-pyridin-3-yl-benzothiazol-2-yl]-urea which
7. 7
   기타was purified by “flash” silica chromatography
8. 8
   세척eluting with 0 to 30% methanol in ethyl acetate

실험 절차

A stirred mixture of 1-(7-Bromo-5-pyridin-3-yl-benzothiazol-2-yl)-3-ethyl-urea (50 mg, 0.133 mmol), 2-fluorobenzeneboronic acid (19 mg, 0.139 mmol), powdered potassium phosphate tribasic (34 mg, 0.160 mmol) and 1,1′-bis(diphenylphosphino)ferrocene palladium(II)chloride complex (16 mg, 0.01995 mmol) in anhydrous 1,4-dioxane (1 ml) and anhydrous methanol (2 ml) was purged with nitrogen for 5 min and heated in a sealed vessel for 16 h at 80° C. After cooling to ambient temperature, the mixture was filtered through kieselguhr. The kieselguhr was thoroughly washed with methanol and the combined filtrates evaporated to dryness in vacuo to give the crude 1-Ethyl-3-[7-(2-fluoro-phenyl)-5-pyridin-3-yl-benzothiazol-2-yl]-urea which was purified by “flash” silica chromatography eluting with 0 to 30% methanol in ethyl acetate. 12 mg of a pale-brown solid was obtained.

출처