Triethylsilane → HCID 22611650, 화합물

HRID 843814노트

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HRID 843814 반응식
[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]

참가 물질

4

반응물 2

HCID 12052TriethylsilaneHCID 22611488HCID 22611488, 화합물

생성물 1

HCID 22611650HCID 22611650, 화합물수율 67.3%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1f433381cdd843f3bb5d3c4c67bb4c18
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06380201B1

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