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

HRID 77790

Reaction equation

HRID 77790 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d302cd83f20244e2983731f1bd9a4106
Source dataset
uspto-grants-2014_09
Patent number
US08841336B2

Linked notes

Loading…