Potassium Carbonate → 5-Nitro-2-(4-(trifluoromethyl)phenyl)pyridine

HRID 1427449Notes

Reaction equation

HRID 1427449 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Cl[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][N:16]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[N+:21]([C:18]1[CH:19]=[CH:20][C:15]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=2)=[N:16][CH:17]=1)([O-:23])=[O:22]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 783082-Chloro-5-nitropyridineHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 679808515-Nitro-2-(4-(trifluoromethyl)phenyl)pyridineYield 37%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

4-(trifluoromethyl)phenylboronic acid (500 mg, 2.63 mmol), 2-chloro-5-nitropyridine (417 mg, 2.63 mmol), potassium carbonate (908 mg, 6.58 mmol) and palladium(II) acetate (23.6 mg, 0.105 mmol) were combined in 1:1 dioxane:water (10 mL). The resulting mixture was stirred at 80° C. for 12 hours. The mixture was filtered and the solution was extracted with ethyl acetate. The organic layer was washed with water, then brine, dried over sodium sulfate, filtered and concentrated. Purification by column chromatography gave 5-nitro-2-(4-(trifluoromethyl)phenyl)pyridine (260 mg, 37%). 1H NMR (400 MHz, CDCl3, δ): 9.47 (s, 1H), 8.51 (d, 1H), 8.14 (d, 2H), 7.72 (d, 1H), 7.65 (d, 2H).

Workup

  1. filtrationThe mixture was filtered
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialbrine, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-581300d2d8c040a7a29bff58f8313c41
Source dataset
uspto-grants-2015_01
Patent number
US08933104B2

Reaction notes

Loading…