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

HRID 1963046ノート

反応式

HRID 1963046 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3163b521c22349678360c62b44e8dd8c
出典データセット
uspto-grants-2013_04
特許番号
US08415336B2

反応ノート

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