Diiodomethane → HCID 67291062, 화합물

HRID 511862

반응식

HRID 511862 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]([NH:14][C@@H:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])=[CH:19][N:18]=2)[CH3:16])=[O:13])=[CH:2]1.[CH2:29]([Zn])C.ICI.Cl.N>ClCCl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C@@H:10]2[CH2:29][C@H:11]2[C:12]([NH:14][C@@H:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]([F:26])([F:28])[F:27])=[CH:19][N:18]=2)[CH3:16])=[O:13])=[CH:2]1

참가 물질

6

반응물 4

HCID 6346DiiodomethaneHCID 12820921Azane;hydrochlorideHCID 67290429(R,E)-3-(1H-indol-3-yl)-N-(1-(5-(2,2,2-trifluoroethoxy)pyridin-2-yl)ethyl)acrylamideHCID 178461638HCID 178461638, 화합물

생성물 1

HCID 67291062HCID 67291062, 화합물수율 3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (R,E)-3-(1H-indol-3-yl)-N-(1-(5-(2,2,2-trifluoroethoxy)pyridin-2-yl)ethyl)acrylamide (600 mg, 1.3 mmol) in dichloromethane (10 mL) was added ethylzinc (4.1 mL, 4.1 mmol, 1.0 M) at room temperature. After being stirred at room temperature for 3 min, diiodomethane (1.8 g, 6.7 mmol) was added to the mixture. The mixture was refluxed at 55° C. with stirring for 18 hours. sat. ammonia hydrochloride aqueous solution was added to the mixture. The organic layer was extracted with ethyl acetate, washed with brine, dried over sodium sulfate. After the filtration to separate solvent and sodium sulfate, the solvent was removed under reduced pressure to give the residue, which was applied to a silica gel chromatography column and eluted with a hexane/ethylacetate=1/1 (v/v) and preparative LC-MS to give 14 mg, (3% yield) of the title compound as a white solid (2:1 mixture of the diastereomers).

후처리

  1. temperatureThe mixture was refluxed at 55° C.
  2. stirringwith stirring for 18 hours
  3. extractionThe organic layer was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter the filtration
  7. customto separate solvent and sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customto give the residue, which
  10. washeluted with a hexane/ethylacetate=1/1 (v/v) and preparative LC-MS

출처 및 근거

ORD 기록
ord-88f13d79354c43b6b4aac5b9fb60f341
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09101616B2

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