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Sodium Carbonate → Methyl-2-(3-fluoro-2-methyl-benzyl)-1-phenyl-indolizine-7-carboxylate

HRID 1963053
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HRID 1963053 반응식
[CH2:1]([C:8]1[CH:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:19][C:20](=O)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=1[CH3:29].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[CH3:17][O:16][C:14]([C:12]1[CH:11]=[CH:10][N:9]2[C:8]([CH:13]=1)=[C:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:20]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=1[CH3:29])=[CH:19]2)=[O:15]
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참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 66731507Methyl 2-benzylisonicotinateHCID 866706671-Bromo-3-(3-fluoro-2-methyl-phenyl)-propan-2-one

생성물 1

HCID 67771873Methyl-2-(3-fluoro-2-methyl-benzyl)-1-phenyl-indolizine-7-carboxylate수율 19.5%

시약·촉매·용매 1

HCID 180Acetone용매

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온도
105 °C

실험 절차

The compound of step 1 (1.555 g, 6.84 mmol) and the compound of example 1, step 2 (1.677 g, 6.84 mmol) were dissolved in 28.5 ml of acetone and the solution was heated to reflux overnight. The mixture was then evaporated to dryness under reduced pressure and the residue dissolved in 28.5 ml of isopropanol. Sodium carbonate (2.176 g, 20.53 mmol) was added and the mixture was heated at 105° C. with stirring for 2 h. The solids were filtered off and the filtrate was evaporated to dryness under reduced pressure. The residue was purified by chromatography on silica gel (cyclohexane/EA, 100:0, then 95:5) to give 0.497 g of the title compound as a yellow solid melting at 55° C.

후처리

  1. temperaturethe solution was heated
  2. temperatureto reflux overnight
  3. customThe mixture was then evaporated to dryness under reduced pressure
  4. dissolutionthe residue dissolved in 28.5 ml of isopropanol
  5. filtrationThe solids were filtered off
  6. customthe filtrate was evaporated to dryness under reduced pressure
  7. customThe residue was purified by chromatography on silica gel (cyclohexane/EA, 100:0

출처 및 근거

ORD 기록
ord-964de9137b6c4c20a8b2cc2ba2995a41
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08415336B2

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