Sodium Carbonate → 4'-(Trifluoromethyl)-[1,1'-biphenyl]-3-amine

HRID 1269599Notes

Reaction equation

HRID 1269599 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[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+]>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>[F:9][C:10]([F:21])([F:20])[C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:8]=[CH:7][CH:6]=[C:4]([NH2:5])[CH:3]=2)=[CH:13][CH:12]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 122713-IodoanilineHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 27827084'-(Trifluoromethyl)-[1,1'-biphenyl]-3-amine

Reagents, catalysts & solvents 3

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

Conditions

Temperature
95 °C

Procedure

To a solution of 3-iodoaniline in DME (40 mL) and water (20 mL), was added para-trifluoromethylphenyl boronic acid (2.6 g, 13.7 mmol) and sodium carbonate (2.5 g, 23.6 mmol). The apparatus was flushed with nitrogen prior to the addition of tetrakis (triphenylphosphine) palladium (0) (0.312 g, 0.27 mmol). The reaction mixture was stirred at 95° C. for 17 h under nitrogen, then allowed to cool to rt and the solvents removed in vacuo. The residue was partitioned between EtOAc (2×75 mL) and water (75 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 white solid (1.33 g).

Workup

  1. customThe apparatus was flushed with nitrogen
  2. temperatureto cool to rt
  3. customthe solvents removed in vacuo
  4. customThe residue was partitioned between EtOAc (2×75 mL) and water (75 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-31376f53df1d4c3fa2813354f0584e52
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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