反応 #69573

反応方程式

2-bromopyridine

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

sodium carbonate

1,2-dimethoxyethane

→

title compound

収率 23.2%

2,3′-Bipyridine-6′-carboxylic acid

収率 23.2%

溶媒

water

ethanol

MeOH

反応条件

後処理

1. 1
   ろ過filtered through Celite®
2. 2
   濃縮The product was concentrated in vacuo
3. 3
   ろ過then filtered through a 20 g SCX cartridge (washed with MeOH, eluted with 1M NH3 in MeOH)
4. 4
   その他evaporated in vacuo
5. 5
   その他The product was triturated with ether
6. 6
   濃縮concentrated under vacuo
7. 7
   workup.ADDITIONThe product was diluted in DCM
8. 8
   workup.ADDITION1 ml of 1M HCl in ether added
9. 9
   濃縮the product was concentrated in vacuo
10. 10
    workup.DISSOLUTIONthen was dissolved in MeCN/DMSO 1:1
11. 11
    その他purified by MDAP
12. 12
    その他The desired fractions were collected
13. 13
    濃縮concentrated under vacuo

実験手順

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).

出典