Silicon tetrachloride → 2-Fluoro-5-(5-isopropyl-tetrazol-1-yl)-3-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester

HRID 77790

반응식

HRID 77790 반응식
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([NH:10][C:11](=O)[CH:12]([CH3:14])[CH3:13])[CH:7]=[C:6]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]=2)[C:5]=1[F:23].[N-:25]=[N+:26]=[N-:27].[Na+].[Si](Cl)(Cl)(Cl)Cl>C(#N)C>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([N:10]2[C:11]([CH:12]([CH3:14])[CH3:13])=[N:27][N:26]=[N:25]2)[CH:7]=[C:6]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]=2)[C:5]=1[F:23]

참가 물질

5

반응물 3

HCID 24816Silicon tetrachlorideHCID 33557Sodium AzideHCID 666642332-Fluoro-5-isobutyrylamino-3-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester

생성물 1

HCID 577498132-Fluoro-5-(5-isopropyl-tetrazol-1-yl)-3-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester수율 90,822.203%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

2-Fluoro-5-isobutyrylamino-3-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester (690 mg, 1.89 mmol), NaN3 (1.1 g, 17 mmol) and SiCl4 (964 mg, 5.67 mmol) were added 20 mL acetonitrile, and the reaction mixture refluxed for 18 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in saturated aqueous NaHCO3, and the resulting mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give 610 g (83%) of 2-fluoro-5-(5-isopropyl-tetrazol-1-yl)-3-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester.

후처리

  1. temperaturethe reaction mixture refluxed for 18 hours
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in saturated aqueous NaHCO3
  4. extractionthe resulting mixture was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d302cd83f20244e2983731f1bd9a4106
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841336B2

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