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 521027ノート

反応式

HRID 521027 の反応式
[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]

参加物

6

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 574072Trimethylboroxine3 回HCID 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

生成物 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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒3 回HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-2776283cd2454dc4a0b7e91101c68120
出典データセット
uspto-grants-2016_05
特許番号
US09328072B2

反応ノート

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