반응 #69573

반응 방정식

2-bromopyridine

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

sodium carbonate

1,2-dimethoxyethane

→

title compound

수율 23.2%

2,3′-Bipyridine-6′-carboxylic acid

수율 23.2%

용매

water

ethanol

MeOH

반응 조건

후처리

1. 1
   여과filtered through Celite®
2. 2
   농축The product was concentrated in vacuo
3. 3
   여과then filtered through a 20 g SCX cartridge (washed with MeOH, eluted with 1M NH3 in MeOH)
4. 4
   기타evaporated in vacuo
5. 5
   기타The product was triturated with ether
6. 6
   농축concentrated under vacuo
7. 7
   workup.ADDITIONThe product was diluted in DCM
8. 8
   workup.ADDITION1 ml of 1M HCl in ether added
9. 9
   농축the product was concentrated in vacuo
10. 10
    workup.DISSOLUTIONthen was dissolved in MeCN/DMSO 1:1
11. 11
    기타purified by MDAP
12. 12
    기타The desired fractions were collected
13. 13
    농축concentrated under vacuo

실험 절차

In a 5 ml microwave vial were added 2-bromopyridine (0.093 ml, 0.949 mmol), methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinecarboxylate (300 mg, 1.139 mmol), bis(triphenylphosphine)palladium(II) chloride (133 mg, 0.190 mmol), sodium carbonate (302 mg, 2.85 mmol), 1,2-dimethoxyethane (1.5 ml), ethanol (1.000 ml) and water (0.500 ml). The reaction mixture was heated for 0.5 hours at 120° C. in the microwave. The mixture was diluted with MeOH and filtered through Celite®. The product was concentrated in vacuo then filtered through a 20 g SCX cartridge (washed with MeOH, eluted with 1M NH3 in MeOH) and evaporated in vacuo. The product was triturated with ether and concentrated under vacuo. The product was diluted in DCM then 1 ml of 1M HCl in ether added and the product was concentrated in vacuo then was dissolved in MeCN/DMSO 1:1 and purified by MDAP. The desired fractions were collected and concentrated under vacuo to give the title compound (44 mg).

출처