Water → Methyl 2-(4-fluorophenoxy)-5-(trifluoromethyl)nicotinate

HRID 1293197Notes

Reaction equation

HRID 1293197 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[N:16]=[CH:15][C:14](I)=[CH:13][C:8]=2[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[F:20][C:21]([F:26])([F:25])C([O-])=O.[Na+].O.ClCCl>CN1CCCC1.[Cu]I>[F:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[N:16]=[CH:15][C:14]([C:21]([F:26])([F:25])[F:20])=[CH:13][C:8]=2[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 517019Sodium TrifluoroacetateHCID 57572293Methyl 2-(4-fluorophenoxy)-5-iodonicotinate

Product 1

HCID 57572267Methyl 2-(4-fluorophenoxy)-5-(trifluoromethyl)nicotinateYield 10.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 84541-MethylpyrrolidineSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of methyl 2-(4-fluorophenoxy)-5-iodonicotinate (step 1, 373 mg, 1.0 mmol), sodium trifluoroacetate (1.36 g, 10 mmol), and copper(I) iodide (960 mg, 5.0 mmol) in 1-methyl-pyrolidine (8.0 mL) was stirred at 160° C. for 16 h under nitrogen atmosphere. The reaction mixture was poured into water (20 mL) and extacted with dichloromethane (50 mL×3). The combined organic extracts were washed with brine (50 mL) and dried (sodium sulfate). After removal of the solvent, the residue was purified by TLC plate developing with hexane/ethyl acetate (1/1) to afford 32 mg (10%) of the title compound: 1H-NMR (CDCl3) δ 8.5 (2H, s), 7.13 (1H, d, J=6.3 Hz), 3.99 (3H, s); MS (ESI) m/z 316 (M+H)+.

Workup

  1. washThe combined organic extracts were washed with brine (50 mL)
  2. dry with materialdried (sodium sulfate)
  3. customAfter removal of the solvent
  4. customthe residue was purified by TLC plate

Sources & evidence

ORD record
ord-a55c78a6b1394766a7589eb15e6231c3
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Reaction notes

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