(E)-1-Bromo-4-(2-iodovinyl)benzene → Ethyl 2-(4-bromophenyl)pyrazolo[1,5-a]pyridine-5-carboxylate

HRID 1475934

반응식

HRID 1475934 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][N+:9](=[N:12]C(=O)C2C=CC=CC=2)[CH2:8][CH:7]=1)=[O:5])[CH3:2].[Br:21][C:22]1[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/I)=[CH:24][CH:23]=1>[Pd](Br)Br.[O-]S(C(F)(F)F)(=O)=O.[Ag+].O1CCOCC1>[Br:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:29]=[C:8]3[CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:11]=[CH:10][N:9]3[N:12]=2)=[CH:24][CH:23]=1

참가 물질

6

반응물 2

HCID 12051842(E)-1-Bromo-4-(2-iodovinyl)benzeneHCID 867112174-Ethoxycarbonyl-N-benzoyliminopyridinium

생성물 1

HCID 68276034Ethyl 2-(4-bromophenyl)pyrazolo[1,5-a]pyridine-5-carboxylate수율 54%

시약·촉매·용매 3

HCID 76223Silver(I) trifluoromethanesulfonate촉매HCID 83469Palladium bromide (PdBr2)촉매HCID 312751,4-Dioxane용매

반응 조건

온도
127.5 °C

실험 절차

Related procedures are described in Org. Lett. 2010, 12, 516): 4-Ethoxycarbonyl-N-benzoyliminopyridinium ylid (JOC 2003, 68, 7119) (3.50 g, 13.0 mmol), para-tris-methoxyphenylphosphine (686 mg, 1.95 mmol), Palladium (II) bromide (173 mg, 0.65 mmol), silver triflate (8.93 g, 39.0 mmol) and (E)-1-Bromo-4-(2-iodovinyl)benzene (Org. Lett. 2008, 10, 5485) (4.02 g, 13.0 mmol) were placed in a 250 mL round bottom flask equipped a with magnetic stirrer. Dioxane (52 mL) was added. The mixture was degassed by bubbling nitrogen for 10 minutes with vigorous stirring and heated to 125-130° C. for 15-20 h. The mixture was then cooled to room temperature, diluted with CH2Cl2, filtered over Celite. The organic layer was then washed with saturated aqueous sodium bicarbonate and the organic phase was concentrated under reduced pressure. The crude product was triturated with methanol to afford 2.40 g (54%) of the title compound. LCMS m/z 345.0, 347.0 (M+H)+, ret. time=3.05 min.

후처리

  1. customwere placed in a 250 mL round bottom flask
  2. customequipped a with magnetic stirrer
  3. customThe mixture was degassed
  4. customby bubbling nitrogen for 10 minutes
  5. temperatureThe mixture was then cooled to room temperature
  6. additiondiluted with CH2Cl2
  7. filtrationfiltered over Celite
  8. washThe organic layer was then washed with saturated aqueous sodium bicarbonate
  9. concentrationthe organic phase was concentrated under reduced pressure
  10. customThe crude product was triturated with methanol

출처 및 근거

ORD 기록
ord-8d9afb91e3aa4b77aed1ebcef3454d46
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018395B2

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