반응 #674829

반응 방정식

X-Phos

ethylboronic acid

dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine

intermediate D70

8-Iodo-3-cyclopropylmethyl-7-chloro[1,2,4]triazolo[4,3-a]pyridine

K2CO3

→

8-Ethyl-3-cyclopropylmethyl-7-chloro[1.2.4]triazolo[4,3-a]pyridine

용매

EtOAc

toluene

반응 조건

후처리

1. 1
   온도After cooling
2. 2
   세척washed with water
3. 3
   기타The organic layer was separated
4. 4
   농축concentrated in vacuo
5. 5
   기타The residue was purified by column chromatography (silica gel; DCM/EtOAc from 100/0 to 20/80 as eluent)
6. 6
   기타The desired fractions were collected
7. 7
   농축concentrated in vacuo
8. 8
   기타to give a residue that
9. 9
   기타was purified by HPLC
10. 10
    기타to yield intermediate D81 (0.053 g, 12.6%)

실험 절차

To a mixture of intermediate D70 (0.6 g, 1.8 mmol) in toluene (14 ml) under a nitrogen atmosphere were added ethylboronic acid (0.665 g, 9 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; X-Phos (0.171 g, 0.36 mmol), palladium(II) acetate (0.04 g, 0.18 mmol) and K2CO3 (0.745 g, 5.396 mmol). The reaction mixture was heated at 100° C. overnight. After cooling, the mixture was diluted with EtOAc and washed with water. The organic layer was separated and concentrated in vacuo. The residue was purified by column chromatography (silica gel; DCM/EtOAc from 100/0 to 20/80 as eluent). The desired fractions were collected and concentrated in vacuo to give a residue that was purified by HPLC to yield intermediate D81 (0.053 g, 12.6%).

출처