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

HRID 337674ノート

反応式

HRID 337674 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-acab8189311743a585f63c67fd3bbb46
出典データセット
uspto-grants-2014_11
特許番号
US08889714B2

反応ノート

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