반응 #683269

반응 방정식

methyl 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

3-chloropyrazin-2-amine

sodium carbonate

→

product

수율 111.1%

methyl 4-(3-aminopyrazin-2-yl)-2-fluorobenzoate

수율 111.1%

용매

DME

반응 조건

후처리

1. 1
   기타The reaction mixture was purged with N2
2. 2
   기타The reaction mixture was partitioned between ethylacetate and water
3. 3
   기타The organic layer was separated
4. 4
   세척washed with brine
5. 5
   건조dried over sodium sulfate
6. 6
   여과filtered
7. 7
   기타evaporated
8. 8
   기타The crude was triturated with DCM
9. 9
   여과Solid observed was filtered
10. 10
    세척washed with ether
11. 11
    기타dried under reduced pressure
12. 12
    기타to provide product as an off white solid
13. 13
    기타Filtrate was purified by flash chromatography
14. 14
    세척eluting with 0-50-80% EtOAc/heptane

실험 절차

To a mixture of 3-chloropyrazin-2-amine (5 g, 38.6 mmol) in DME (160 mL) and aq. 2 M sodium carbonate (40 mL, 80 mmol) was added methyl 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (12.97 g, 46.3 mmol) followed by PdCl2(dppf)-CH2Cl2 adduct (3.15 g, 3.86 mmol). The reaction mixture was purged with N2 and heated in an oil bath at 100° C. for 3-4 h. The reaction mixture was partitioned between ethylacetate and water. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered and evaporated. The crude was triturated with DCM. Solid observed was filtered, washed with ether and dried under reduced pressure to provide product as an off white solid. Filtrate was purified by flash chromatography eluting with 0-50-80% EtOAc/heptane to provide 10.6 g of product in 93% yield. LCMS (m/z): 248.1 (MH+), 0.563 min.

출처