Diiodomethane → HCID 67291062、化合物

HRID 511862

反応式

HRID 511862 の反応式
[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

参加物

6

反応物 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、化合物

生成物 1

HCID 67291062HCID 67291062、化合物収率 3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-88f13d79354c43b6b4aac5b9fb60f341
出典データセット
uspto-grants-2015_08
特許番号
US09101616B2

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