Sodium Carbonate → 2-Bromo-6-(4-(trifluoromethyl)phenyl)pyridine

HRID 1269584Notes

Reaction equation

HRID 1269584 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[F:9][C:10]([F:21])([F:20])[C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:14]2[CH:15]=[CH:16][C:11]([C:10]([F:21])([F:20])[F:9])=[CH:12][CH:13]=2)[N:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 122742,6-DibromopyridineHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 184483252-Bromo-6-(4-(trifluoromethyl)phenyl)pyridineYield 22%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 2,6-dibromopyridine (1.25 g, 5.28 mmol) in dimethoxyethane (100 mL) and water (50 mL), was added 4-trifluromethylphenylboronic acid (1 g, 5.27 mmol) and sodium carbonate (1.45 g, 13.7 mmol). The resulting mixture was flushed with nitrogen prior to addition of tetrakis(triphenylphosphine) palladium (0) (60 mg, 0.05 mmol). The reaction mixture was heated to reflux under nitrogen for 5 h and then allowed to attain room temperature. The solvents were removed in vacuo and the residue diluted with water (50 mL) and then extracted EtOAc (2×100 mL). The organic solution was dried (MgSO4), filtered and the solvents removed in vacuo. Purification by Biotage™ chromatography (Silica, 90 g) eluting with 4:1 cyclohexane:chloroform afforded the title compound as a white solid (0.35 g).

Workup

  1. customThe resulting mixture was flushed with nitrogen
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux under nitrogen for 5 h
  4. customto attain room temperature
  5. customThe solvents were removed in vacuo
  6. additionthe residue diluted with water (50 mL)
  7. dry with materialThe organic solution was dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvents removed in vacuo
  10. customPurification by Biotage™ chromatography (Silica, 90 g)
  11. washeluting with 4:1 cyclohexane

Sources & evidence

ORD record
ord-594169d58f4940de9db4a045ea903d6f
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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