Pyridine → HCID 58374162, compound

HRID 1804508Notes

Reaction equation

HRID 1804508 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 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 3-isobutyl-4-(trifluoromethyl)isoxazole-5-carboxylic acid (0.200 g, 0.843 mmol) and pyridine (0.082 mL, 1.01 mmol) in dichloromethane (8 mL) at room temperature was added 2,4,6-trifluoro-1,3,5-triazine (cyanuric fluoride) (0.085 mL, 1.01 mmol). The reaction mixture was stirred at room temperature overnight. The heterogeneous reaction 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 anhydrous sodium sulfate and concentrated to afford 3-isobutyl-4-(trifluoromethyl)isoxazole-5-carbonyl fluoride (0.130 g, 0.544 mmol, 65% yield) as a yellow solid. The product had an HPLC ret. time=2.51 min. (corresponding to the 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. concentrationconcentrated

Sources & evidence

ORD record
ord-ad10d95325be4f2e9f2e7ab07c898492
Source dataset
uspto-grants-2013_01
Patent number
US08354398B2

Reaction notes

Loading…