Pyridine → HCID 58374067, compound

HRID 1506281Notes

Reaction equation

HRID 1506281 reaction equation
[C:1]1([C:7]2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]([OH:18])=O)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[F:25]C1N=C(F)N=C(F)N=1>ClCCl>[C:1]1([C:7]2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]([F:25])=[O:18])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 583740941236188-80-9

Product 1

HCID 58374067HCID 58374067, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 3-phenyl-4-(trifluoromethyl)isoxazole-5-carboxylic acid (Intermediate I-3D, 3.00 g, 11.7 mmol) and pyridine (1.13 mL, 14.0 mmol) in dichloromethane (100 mL) at room temperature was added 2,4,6-trifluoro-1,3,5-triazine (cyanuric fluoride) (1.18 mL, 14.0 mmol). The reaction mixture was stirred at room temperature overnight, diluted with dichloromethane (300 mL), washed with an ice-cold solution of 0.5N aqueous hydrochloric acid (2×100 mL), and the organic layer was collected. The aqueous layer was back-extracted with dichloromethane (200 mL), and the combined organic layers were dried anhydrous sodium sulfate and concentrated to afford 3-phenyl-4-(trifluoromethyl)isoxazole-5-carbonyl fluoride (2.91 g, 11.2 mmol, 96% yield) as a yellow, viscous oil. The product was found to react readily with methanol and on analysis was characterized as the methyl ester, which had an HPLC ret. time=2.56 min. —(Condition A); LC/MS M+1=272.3 (methyl ester).

Workup

  1. washwashed with an ice-cold solution of 0.5N aqueous hydrochloric acid (2×100 mL)
  2. customthe organic layer was collected
  3. extractionThe aqueous layer was back-extracted with dichloromethane (200 mL)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-468bf760c07249fb9f8333a6a21546e8
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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