Triethylsilane → HCID 22611650、化合物

HRID 1737768ノート

反応式

HRID 1737768 の反応式
[Cl:1][C:2]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[C:16]1[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH:21]=1)=[O:5].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH:16]1[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]1)=[O:5]

参加物

4

反応物 2

HCID 12052TriethylsilaneHCID 22611488HCID 22611488、化合物

生成物 1

HCID 22611650HCID 22611650、化合物収率 67.3%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

To a solution of 0.40 gm (1.04 mMol) 5-(2-chloro-4-fluorobenzoyl)amino-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole in 5.2 mL trifluoroacetic acid were added 0.208 mL (1.3 mMol) triethylsilane and the reaction mixture was stirred at ambient. After 2 hours, the reaction mixture was concentrated under reduced pressure. To the residue was added 2N sodium hydroxide and the aqueous was extracted with dichloromethane. The combined organic extracts were washed with 2N sodium hydroxide, dried over sodium sulfate and then concentrated under reduced pressure to give an orange foam. The foam was subjected to radial chromatography (2 mm silica), eluting with 100:10:1 dichloromethane:methanol:ammonium hydroxide. The residue was crystallized from ethyl acetate/hexanes to give 0.27 gm (67.3%) of the title compound as a burnt orange powder.

後処理

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added 2N sodium hydroxide
  3. extractionthe aqueous was extracted with dichloromethane
  4. washThe combined organic extracts were washed with 2N sodium hydroxide
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give an orange foam
  8. washeluting with 100:10:1 dichloromethane
  9. customThe residue was crystallized from ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-e670468d94a34c188fab4b9d1d6c108c
出典データセット
uspto-grants-1999_10
特許番号
US05962474

反応ノート

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