Ethanol → 3-(2-Nitro-4-(trifluoromethyl)phenyl)pyridine

HRID 1042685Notes

Reaction equation

HRID 1042685 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=1[NH2:21].C(=O)([O-])[O-:23].[Na+].[Na+].C(O)C.[OH2:31]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[N+:21]([C:12]1[CH:13]=[C:14]([C:17]([F:20])([F:19])[F:18])[CH:15]=[CH:16][C:11]=1[C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)([O-:23])=[O:31]

Participants

8

Reactant 5

HCID 702EthanolHCID 962WaterHCID 10340Sodium CarbonateHCID 679892-Bromo-5-(trifluoromethyl)benzenamineHCID 27343783-Pyridinylboronic acid

Product 1

HCID 463167623-(2-Nitro-4-(trifluoromethyl)phenyl)pyridine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of pyridin-3-ylboronic acid (0.99 g, 8.1 mmol), 2-bromo-5-(trifluoromethyl)benzenamine (1.2 ml, 8.1 mmol), tetrakis(triphenylphosphine)palladium (0.28 g, 0.24 mmol), sodium carbonate (2.0 M solution in water, 8.0 ml, 16 mmol), 4 ml ethanol, and 20 ml toluene was heated to 90° C. under nitrogen with a water-cooled reflux condenser. After 12 h, mixture was cooled to ambient temperature, and was partitioned between EtOAc and 1N NaOH. The organic layer was washed once with brine, dried with Na2SO4, filtered, and concentrated to give a brown oil, which was further purified by silica gel chromatography (EtOAc/hexanes) to give the desired product as a waxy orange solid. MS (m/z): 269.0 (M+H)−. Calc'd for C12H7F3N2O2: 268.19.

Workup

  1. temperaturecooled
  2. temperaturereflux condenser
  3. customwas partitioned between EtOAc and 1N NaOH
  4. washThe organic layer was washed once with brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a brown oil, which
  9. customwas further purified by silica gel chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-8939bd5cab6444898f34cf7b2157f512
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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