Ethanol → 1-(1,1-Dimethylethyl) 3-ethyl 5,6-dihydro-4,4'-bipyridine-1,3(2H)-dicarboxylate

HRID 337674노트

반응식

HRID 337674 반응식
C(O)C.FC(F)(F)S(O[C:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][C:11]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24])(=O)=O.[N:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[N:13]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15][C:10]([C:33]2[CH:34]=[CH:35][N:30]=[CH:31][CH:32]=2)=[C:11]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:12]1

참가 물질

7

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 222284091-(tert-Butyl) 3-ethyl 4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1,3(2H)-dicarboxylate

생성물 1

HCID 669000221-(1,1-Dimethylethyl) 3-ethyl 5,6-dihydro-4,4'-bipyridine-1,3(2H)-dicarboxylate

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

To a 1:1 (v/v) ethanol:toluene solution (0.18 M) of 1-(1,1-dimethylethyl) 3-ethyl 4-{[(trifluoromethyl)sulfonyl]oxy}-5,6-dihydro-1,3(2H)-pyridinedicarboxylate (1 eq.) and 4-pyridinylboronic acid (1.1 eq.) was added sodium carbonate (2 M aq. solution, 2.6 eq.). The suspension was evacuated and back-filled with N2. Finally, tetrakis(triphenylphosphine)palladium(0) (0.04 eq.) was added in one rapid portion and the reaction suspension was heated at 80° C. for 18 h. The reaction was then quenched with sat. aq. NH4Cl and extracted with EtOAc. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of column chromatography (SiO2, 80:20 (v/v) Hex:EtOAc→ EtOAc) afforded the title compound as a golden yellow oil.

후처리

  1. customThe suspension was evacuated
  2. additionback-filled with N2
  3. customThe reaction was then quenched with sat. aq. NH4Cl
  4. extractionextracted with EtOAc
  5. washThe combined organic extracts were washed further with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo
  9. customPurification of the crude product
  10. customthus obtained by way of column chromatography (SiO2, 80:20 (v/v) Hex:EtOAc→ EtOAc)

출처 및 근거

ORD 기록
ord-acab8189311743a585f63c67fd3bbb46
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889714B2

반응 노트

불러오는 중…