Water → Methyl 2'-fluoro-5-(5-methylpyridin-2-yl)-6'-(trifluoromethyl)biphenyl-3-carboxylate

HRID 2278761Notes

Reaction equation

HRID 2278761 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16](B3OC(C)(C)C(C)(C)O3)[CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[N:6][CH:7]=1.Br[C:28]1[C:33]([C:34]([F:37])([F:36])[F:35])=[CH:32][CH:31]=[CH:30][C:29]=1[F:38].C(=O)([O-])[O-].[Cs+].[Cs+].O.CN(C)C=O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:38][C:29]1[CH:30]=[CH:31][CH:32]=[C:33]([C:34]([F:35])([F:36])[F:37])[C:28]=1[C:16]1[CH:17]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=2)[CH:9]=[C:10]([C:11]([O:13][CH3:14])=[O:12])[CH:15]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 5178472-Bromo-3-fluorobenzotrifluorideHCID 59432564Methyl 3-(5-methylpyridin-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Product 1

HCID 67303854Methyl 2'-fluoro-5-(5-methylpyridin-2-yl)-6'-(trifluoromethyl)biphenyl-3-carboxylate

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

In a 5 mL microwave vial, methyl 3-(5-methylpyridin-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (300.0 mg, 0.8493 mmol), 2-bromo-1-fluoro-3-(trifluoromethyl)benzene (412.8 mg, 1.699 mmol), cesium carbonate (1384 mg, 4.247 mmol), tetra-n-butylammonium iodide (313.7 mg, 0.8493 mmol), and POPd (42.61 mg, 0.08493 mmol) were dissolved in Water (0.6 mL, 40 mmol) and N,N-dimethylformamide (3 mL, 40 mmol). The reaction mixture was microwaved for 10 mins at 150 degrees. The reaction mixture was extracted with ethylacetate and washed repeatedly with brine. The solvent removed under reduced pressure (yellow oil) and used in the next reaction without further purification.

Workup

  1. customThe reaction mixture was microwaved for 10 mins at 150 degrees
  2. extractionThe reaction mixture was extracted with ethylacetate
  3. washwashed repeatedly with brine
  4. customThe solvent removed under reduced pressure (yellow oil)
  5. customused in the next reaction without further purification

Sources & evidence

ORD record
ord-5c4152fa16cb4689ad68949adf930429
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

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