Pyridine → HCID 58374162, compound

HRID 1948464Notes

Reaction equation

HRID 1948464 reaction equation
[CH2:1]([C:5]1[C:9]([C:10]([F:13])([F:12])[F:11])=[C:8]([C:14]([OH:16])=O)[O:7][N:6]=1)[CH:2]([CH3:4])[CH3:3].N1C=CC=CC=1.[F:23]C1N=C(F)N=C(F)N=1>ClCCl>[CH2:1]([C:5]1[C:9]([C:10]([F:13])([F:12])[F:11])=[C:8]([C:14]([F:23])=[O:16])[O:7][N:6]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 66955474HCID 66955474, compound

Product 1

HCID 58374162HCID 58374162, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 3-isobutyl-4-(trifluoromethyl)isoxazole-5-carboxylic acid (0.070 g, 0.295 mmol) and pyridine (0.029 mL, 0.354 mmol) in dichloromethane (2.5 mL) at room temperature was added 2,4,6-trifluoro-1,3,5-triazine (cyanuric fluoride) (0.030 mL, 0.354 mmol). The reaction mixture was stirred at room temperature for 5.5 h. The heterogeneous reaction was complete by HPLC and was diluted with dichloromethane, washed with an ice-cold solution of 0.5N aqueous hydrochloric acid (2×), and the organic layer was collected. The aqueous layer was back-extracted with dichloromethane, and the combined organic layers were dried with anhydrous sodium sulfate and concentrated to afford 3-isobutyl-4-(trifluoromethyl)isoxazole-5-carbonyl fluoride (0.050 g, 0.209 mmol, 70.8% yield) as a yellow solid. The product had an HPLC ret. time=2.52 min (methyl ester)-Column: CHROMOLITH® SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA.

Workup

  1. customThe heterogeneous reaction
  2. washwashed with an ice-cold solution of 0.5N aqueous hydrochloric acid (2×)
  3. customthe organic layer was collected
  4. extractionThe aqueous layer was back-extracted with dichloromethane
  5. dry with materialthe combined organic layers were dried with anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7258fb7002e44f77a7eec93a013bcaf1
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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