2-Bromopyridine → [2,3'-Bipyridine]-6'-carboxylic acid

HRID 41295노트

반응식

HRID 41295 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:16]2[CH:17]=[CH:18][C:19]([C:22]([O:24]C)=[O:23])=[N:20][CH:21]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>CO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C(O)C>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:16]1[CH:21]=[N:20][C:19]([C:22]([OH:24])=[O:23])=[CH:18][CH:17]=1

참가 물질

9

반응물 4

HCID 79732-BromopyridineHCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 467386632-Methoxycarbonyl-5-pyridineboronic acid, pinacol ester

생성물 1

HCID 57358853[2,3'-Bipyridine]-6'-carboxylic acid수율 23.2%

시약·촉매·용매 4

HCID 178418476HCID 178418476, 화합물촉매HCID 702Ethanol용매HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
120 °C

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).

후처리

  1. filtrationfiltered through Celite®
  2. concentrationThe product was concentrated in vacuo
  3. filtrationthen filtered through a 20 g SCX cartridge (washed with MeOH, eluted with 1M NH3 in MeOH)
  4. customevaporated in vacuo
  5. customThe product was triturated with ether
  6. concentrationconcentrated under vacuo
  7. additionThe product was diluted in DCM
  8. addition1 ml of 1M HCl in ether added
  9. concentrationthe product was concentrated in vacuo
  10. dissolutionthen was dissolved in MeCN/DMSO 1:1
  11. custompurified by MDAP
  12. customThe desired fractions were collected
  13. concentrationconcentrated under vacuo

출처 및 근거

ORD 기록
ord-9ecab71c57fd40988bfeff16b7449608
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530478B2

반응 노트

불러오는 중…