Sodium Carbonate → 2-Methyl-4'-(trifluoromethyl)biphenyl-3-amine

HRID 1269612Notes

Reaction equation

HRID 1269612 reaction equation
Br[C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[F:10][C:11]([F:22])([F:21])[C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[CH3:9][C:3]1[C:4]([NH2:5])=[CH:6][CH:7]=[CH:8][C:2]=1[C:15]1[CH:16]=[CH:17][C:12]([C:11]([F:22])([F:21])[F:10])=[CH:13][CH:14]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 1235383-Bromo-o-toluidineHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 184483532-Methyl-4'-(trifluoromethyl)biphenyl-3-amineYield 79%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of 3-bromo-2-methylaniline (1.19 g, 6.4 mmol) in DME (30 mL) and water (15 mL) was added para-trifluoromethylphenyl boronic acid (1.82 g, 9.6 mmol) and sodium carbonate (1.76 g, 16.6 mmol). The apparatus was flushed with nitrogen prior to the addition of tetrakis (triphenylphosphine) palladium (0) (0.22 g, 0.19 mmol). The resultant mixture was heated to reflux and stirred under nitrogen for 17 h, then allowed to cool to room temperature and the solvents removed in vacuo. The residue was partitioned between EtOAc (2×60 mL) and water (60 mL). The organic solution was dried (MgSO4) and the solvent was removed in vacuo. Purification by Biotage™ chromatography (90 g Silica column) eluted with 1:4 EtOAc:cyclohexane afforded the title compound as a cream coloured solid (1.27 g).

Workup

  1. customThe apparatus was flushed with nitrogen
  2. temperatureto reflux
  3. customthe solvents removed in vacuo
  4. customThe residue was partitioned between EtOAc (2×60 mL) and water (60 mL)
  5. dry with materialThe organic solution was dried (MgSO4)
  6. customthe solvent was removed in vacuo
  7. customPurification by Biotage™ chromatography (90 g Silica column)
  8. washeluted with 1:4 EtOAc

Sources & evidence

ORD record
ord-ae6bae936ee84345acf5256d9c52c802
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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