반응 #169651

반응 방정식

(6-bromo-pyridin-3-yl)-methanol

cesium carbonate

2-picoline-5-boronic acid pinacol ester

→

(6′-methyl-2,3′-bipyridin-5-yl)methanol

용매

dichloromethane

THF

dichloromethane

반응 조건

후처리

1. 1
   온도cooled to rt
2. 2
   세척The organic solution was washed with water
3. 3
   건조dried over sodium sulfate
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo
6. 6
   농축The aqueous fraction was concentrated in vacuo
7. 7
   기타triturated 3× with 20% methanol in dichloromethane
8. 8
   여과collected via filtration
9. 9
   기타The combined solids were purified via silica gel chromatography
10. 10
    세척eluting with 100% ethyl acetate

실험 절차

To a solution of (6-bromo-pyridin-3-yl)-methanol (0.614 g, 3.27 mmol) in 10 mL of THF under an atmosphere of nitrogen was added cesium carbonate (3.27 mL, 2 N aqueous, 6.53 mmol), 2-picoline-5-boronic acid pinacol ester (0.477 g, 2.18 mmol), and [1,1′-bis(diphenylphosphino)-ferrocene]dichloro-palladium(II), 1:1 complex with dichloromethane (0.178 g, 0.218 mmol). The reaction was heated at 85° C. for 1 h, cooled to rt, and diluted with dichloromethane. The organic solution was washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo. The aqueous fraction was concentrated in vacuo, triturated 3× with 20% methanol in dichloromethane, and collected via filtration. The combined solids were purified via silica gel chromatography, eluting with 100% ethyl acetate to provide (6′-methyl-2,3′-bipyridin-5-yl)methanol that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 201.1 for [M+H]+.

출처