Potassium Phosphate, Tribasic → 4-[[5-methoxy-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine

HRID 623690Notes

Reaction equation

HRID 623690 reaction equation
Br[CH2:2][C:3]1[C:7]([O:8][CH3:9])=[N:6][N:5]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[N:4]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[F:28][C:29]([F:46])([F:45])[C:30]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[CH:32][N:31]=1>O1CCCC1.O.O.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>[CH3:9][O:8][C:7]1[C:3]([CH2:2][C:34]2[CH:33]=[CH:32][N:31]=[C:30]([C:29]([F:46])([F:45])[F:28])[CH:35]=2)=[N:4][N:5]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[N:6]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 457857082-(Trifluoromethyl)pyridine-4-boronic acid, pinacol esterHCID 901093144-(bromomethyl)-5-methoxy-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole2×

Product 1

HCID 901098604-[[5-methoxy-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazol-4-yl]methyl]-2-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 4-(bromomethyl)-5-methoxy-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole (i.e. the product of Step D, 0.525 g, 66 weight %, 1.0 mmol) in tetrahydrofuran/water (3:1, 4 mL total), was added tetrakis(triphenylphosphine)palladium(0) (0.059 g, 0.05 mmol), potassium phosphate tribasic (0.43 g, 2.0 mmol) and 2-(trifluoromethyl)pyridine-4-boronic acid pinacol ester (0.42 g, 1.5 mmol). The mixture was heated to reflux and stirred for 17 h. The reaction mixture was diluted with water (20 mL) and extracted twice with ethyl acetate (25 mL, 15 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel eluting with 10% ethyl acetate in hexanes to afford the title compound (0.12 g) as a pale yellow solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. extractionextracted twice with ethyl acetate (25 mL, 15 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by chromatography on silica gel eluting with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-0279a058701e484a924658a90a89f683
Source dataset
uspto-grants-2016_04
Patent number
US09302999B2

Reaction notes

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