Sodium Carbonate → 1-Cyclohexyl-2-(3-fluoro-2-methyl-benzyl)indolizine

HRID 1963046노트

반응식

HRID 1963046 반응식
[CH:1]1([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.Br[CH2:15][C:16](=O)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:19]=1[CH3:25].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[CH:1]1([C:7]2[C:16]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:19]=3[CH3:25])=[CH:15][N:9]3[C:8]=2[CH:13]=[CH:12][CH:11]=[CH:10]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 677737612-(Cyclohex-2-en-1-ylmethyl)-pyridineHCID 866706671-Bromo-3-(3-fluoro-2-methyl-phenyl)-propan-2-one

생성물 1

HCID 677720901-Cyclohexyl-2-(3-fluoro-2-methyl-benzyl)indolizine수율 64.2%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

The compound of step 1 (0.415 g, 2.37 mmol) and the compound of step 2 of example 1 (0.58 g, 2.37 mmol) were dissolved in 15 ml of acetone and the solution was stirred under reflux for 36 h. The solution was evaporated to dryness and the solid (0.92 g) dissolved in 10 ml of isopropanol. Sodium carbonate (0.70 g, 6.57 mmol) was added, the mixture was stirred under reflux for 2 h and then evaporated to dryness under reduced pressure. The residue was taken up in DCM and water, and the aqueous phase was extracted twice with DCM. The combined organic phases were dried over sodium sulfate, filtered and evaporated to dryness under reduced pressure. The residue was purified by chromatography on silica gel (HEP/EA, 100:0, then 70:30) to give 0.489 g of the title compound as a thick yellow oil.

후처리

  1. temperatureunder reflux for 36 h
  2. customThe solution was evaporated to dryness
  3. dissolutionthe solid (0.92 g) dissolved in 10 ml of isopropanol
  4. stirringthe mixture was stirred
  5. temperatureunder reflux for 2 h
  6. customevaporated to dryness under reduced pressure
  7. extractionwater, and the aqueous phase was extracted twice with DCM
  8. dry with materialThe combined organic phases were dried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated to dryness under reduced pressure
  11. customThe residue was purified by chromatography on silica gel (HEP/EA, 100:0

출처 및 근거

ORD 기록
ord-3163b521c22349678360c62b44e8dd8c
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415336B2

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