Water → 2',3'-Difluoro-5-(5-methylpyridin-2-yl)biphenyl-3-carboxylic acid

HRID 2278756Notes

Reaction equation

HRID 2278756 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]C)=[O:12])=[N:6][CH:7]=1.Br[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[C:29]=1[F:35].C(=O)([O-])[O-].[Cs+].[Cs+].O.CN(C)C=O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:34][C:30]1[C:29]([F:35])=[CH:28][CH:33]=[CH:32][C:31]=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]([OH:13])=[O:12])[CH:15]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 27332601-Bromo-2,3-difluorobenzeneHCID 59432564Methyl 3-(5-methylpyridin-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Product 1

HCID 584493602',3'-Difluoro-5-(5-methylpyridin-2-yl)biphenyl-3-carboxylic acid

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 (250 mg, 0.71 mmol), 1-bromo-2,3-difluorobenzene (273.2 mg, 1.416 mmol), cesium carbonate (1153 mg, 3.539 mmol), tetra-n-butylammonium iodide (261.4 mg, 0.7078 mmol), and POPd (35.51 mg, 0.07078 mmol) were dissolved in Water (0.5 mL, 30 mmol) and N,N-dimethylformamide (3 mL, 30 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 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
  5. customused in the next reaction without further purification

Sources & evidence

ORD record
ord-328ed60727c445bc99ed83a823ba5d37
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

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