Potassium Phosphate, Tribasic → cis-2,2,2-Trifluoro-1-(6-methyl-2,3,4,4a,9,9a-hexahydro-indeno[2,1-b]pyridin-1-yl)-ethanone

HRID 455370노트

반응식

HRID 455370 반응식
[F:1][C:2]([F:27])([F:26])[C:3]([N:5]1[CH2:10][CH2:9][CH2:8][C@@H:7]2[C:11]3[CH:12]=[C:13](OS(C(F)(F)F)(=O)=O)[CH:14]=[CH:15][C:16]=3[CH2:17][C@H:6]12)=[O:4].[CH3:28]B1OB(C)OB(C)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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.O1CCOCC1>[F:1][C:2]([F:27])([F:26])[C:3]([N:5]1[CH2:10][CH2:9][CH2:8][C@@H:7]2[C:11]3[CH:12]=[C:13]([CH3:28])[CH:14]=[CH:15][C:16]=3[CH2:17][C@H:6]12)=[O:4]

참가 물질

6

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 574072Trimethylboroxine3회HCID 58294405trifluoro-methanesulfonic acid cis-1-(2,2,2-trifluoro-acetyl)-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridin-6-yl ester

생성물 1

HCID 58294400cis-2,2,2-Trifluoro-1-(6-methyl-2,3,4,4a,9,9a-hexahydro-indeno[2,1-b]pyridin-1-yl)-ethanone

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매3회HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

Tetrakis(triphenylphosphine)palladium(0) (17 mg) is added to a flask charged with a stir bar, trifluoromethanesulfonic acid cis-1-(2,2,2-trifluoro-acetyl)-2,3,4,4a,9,9a-hexahydro-1H-indeno[2,1-b]pyridin-6-yl ester (200 mg), trimethylboroxine (81 μL), K3PO4 (0.15 g), and 1,4-dioxane (4 mL) under argon atmosphere at room temperature. The reaction mixture is heated to 100° C. and stirred at this temperature overnight. Another portion of trimethylboroxine (40 μL) and tetrakis(triphenylphosphine)palladium(0) (17 mg) is then added and stirring is continued at 100° C. The addition of further amounts of trimethylboroxine and tetrakis(triphenylphosphine)palladium(0) is repeated after each 6 h of stirring until the starting material is completely consumed. After cooling to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The combined extract is dried (Na2SO4) and concentrated and the residue is chromatographed on silica gel (dichloromethane/methanol 1:0→9:1) to give the title compound. Yield: 50 mg (37% of theory); LC (method 1): tR=4.62 min; Mass spectrum (ESI+): m/z=284 [M+H]+.

후처리

  1. additioncharged with a stir bar
  2. customat room temperature
  3. stirringstirring
  4. customis continued at 100° C
  5. waitis repeated after each 6 h
  6. stirringof stirring until the starting material
  7. customis completely consumed
  8. temperatureAfter cooling to room temperature
  9. additionwater is added
  10. extractionthe resulting mixture is extracted with ethyl acetate
  11. extractionThe combined extract
  12. dry with materialis dried (Na2SO4)
  13. concentrationconcentrated
  14. customthe residue is chromatographed on silica gel (dichloromethane/methanol 1:0→9:1)

출처 및 근거

ORD 기록
ord-40dc514852b947d6925c3791a2dfe25a
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497281B2

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