Pyridine → HCID 58537229, compound

HRID 1804483Notes

Reaction equation

HRID 1804483 reaction equation
[F:1][C:2]([C:6]1[C:7]([C:17]([OH:19])=O)=[N:8][O:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([F:5])[CH2:3][CH3:4].N1C=CC=CC=1.N1C(F)=NC(F)=NC=1[F:28]>ClCCl>[F:1][C:2]([C:6]1[C:7]([C:17]([F:28])=[O:19])=[N:8][O:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([F:5])[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 58537205HCID 58537205, compound

Product 1

HCID 58537229HCID 58537229, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-(1,1-difluoropropyl)-5-phenylisoxazole-3-carboxylic acid (8.4 mg, 0.031 mmol) and pyridine (3.05 μL, 0.038 mmol) in dichloromethane (1 mL) was added cyanuric fluoride (3.18 μL, 0.038 mmol), and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with dichloromethane (2 mL) and washed with ice-water (2×1 mL). The aqueous layer was extracted with dichloromethane (2×1 mL), and the combined organic layers were washed brine (1 mL) and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded 4-(1,1-difluoropropyl)-5-phenylisoxazole-3-carbonyl fluoride (7.2 mg).

Workup

  1. washwashed with ice-water (2×1 mL)
  2. extractionThe aqueous layer was extracted with dichloromethane (2×1 mL)
  3. washthe combined organic layers were washed brine (1 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-ba2271c28ba24cf88acedc3214030d4e
Source dataset
uspto-grants-2013_01
Patent number
US08354398B2

Reaction notes

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