Dimethylformamide → Methyl 4-(5,5,5-trifluoro-2-(2-methyl-4-(5-(trifluoromethyl)pyridin-2-yl)phenyl)pentyl)benzoate

HRID 1520247Notes

Reaction equation

HRID 1520247 reaction equation
[F:1][C:2]([F:34])([F:33])[CH2:3][CH2:4][CH:5](NC1C=CC(C(OC)=O)=CC=1)[C:6]1[CH:11]=[CH:10][C:9](B2OC(C)(C)C(C)(C)O2)=[CH:8][C:7]=1[CH3:21].Br[C:36]1[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][N:37]=1.CO[C:48]1[CH:53]=[CH:52][CH:51]=[C:50](OC)[C:49]=1[C:56]1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[C:75](=[O:78])([O-])[O-:76].[Cs+].[Cs+].[CH3:81]N(C)C=O>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[F:34][C:2]([F:1])([F:33])[CH2:3][CH2:4][CH:5]([C:6]1[CH:11]=[CH:10][C:9]([C:36]2[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][N:37]=2)=[CH:8][C:7]=1[CH3:21])[CH2:56][C:49]1[CH:50]=[CH:51][C:52]([C:75]([O:76][CH3:81])=[O:78])=[CH:53][CH:48]=1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 27364342-Bromo-5-(trifluoromethyl)pyridineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 131733097Methyl 4-((4,4,4-trifluoro-1-(2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butyl)amino)benzoate

Product 1

HCID 117839891Methyl 4-(5,5,5-trifluoro-2-(2-methyl-4-(5-(trifluoromethyl)pyridin-2-yl)phenyl)pentyl)benzoate

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

A reaction mixture of methyl 4-((4,4,4-trifluoro-1-(2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butyl)amino)benzoate (14.3 g) obtained in step F, 2-bromo-5-(trifluoromethyl)pyridine (7.45 g), tris(dibenzylideneacetone)dipalladium (1.37 g), 2,6-dimethoxy-2′ (dicyclohexylphosphino)biphenyl (2.46 g), cesium carbonate (29.3 g), dimethylformamide (100 mL) and water (25 ml) was stirred at 80° C. overnight under a nitrogen atmosphere. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (13.6 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4f71309b11674efcb4c117bc129253f1
Source dataset
uspto-grants-2015_07
Patent number
US09073864B2

Reaction notes

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