Pyridine → HCID 58537232, compound

HRID 1804492Notes

Reaction equation

HRID 1804492 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:7][O:8][C:9]=1[C:10](O)=[O:11])=[O:4].N1C=CC=CC=1.N1C(F)=NC(F)=NC=1[F:27]>C(Cl)Cl>[F:27][C:10]([C:9]1[O:8][N:7]=[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]=1[C:3]([O:2][CH3:1])=[O:4])=[O:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 58537227HCID 58537227, compound

Product 1

HCID 58537232HCID 58537232, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(methoxycarbonyl)-3-phenylisoxazole-5-carboxylic acid (100 mg, 0.405 mmol) and pyridine (0.039 mL, 0.485 mmol) in DCM (4 mL) at rt was added cyanuric fluoride (0.041 mL, 0.485 mmol) and the reaction mixture was stirred at rt for 2 hr. The reaction mixture was diluted with dichloromethane (20 ml) and washed with ice-cold 0.5N HCl (20 mL). The aqueous layer was extracted with DCM (10 mL) and the combined organic layers were dried (MgSO4), filtered and concentrated to afford methyl 5-(fluorocarbonyl)-3-phenylisoxazole-4-carboxylate (100 mg, 0.401 mmol, 99% yield) as a colorless oil. The compound was found to react readily with methanol and was characterized as the methyl ester. HPLC retention time=1.59 minutes (PHENOMENEX® Luna 4.6×30 mm S-5 ODS column) eluting with 10-90% aqueous methanol+0.1% TFA over a 2 minute gradient. MS: (M+H)=262.15 (methyl ester).

Workup

  1. washwashed with ice-cold 0.5N HCl (20 mL)
  2. extractionThe aqueous layer was extracted with DCM (10 mL)
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0375e9e33f2243b69114f44f31c70ad6
Source dataset
uspto-grants-2013_01
Patent number
US08354398B2

Reaction notes

Loading…