Methyl 3-bromo-5-(2,2,2-trifluoro-1-hydroxyethyl)benzoate → Methyl 2'-cyano-4'-methyl-5-(2,2,2-trifluoro-1-hydroxyethyl)biphenyl-3-carboxylate

HRID 1845305Notes

Reaction equation

HRID 1845305 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH:12]([OH:17])[C:13]([F:16])([F:15])[F:14])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:18][C:19]1[CH:20]=[CH:21][C:22](B2OC(C)(C)C(C)(C)O2)=[C:23]([CH:26]=1)[C:24]#[N:25]>CN(C)C=O.C1(C)C=CC=CC=1.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>[C:24]([C:23]1[CH:26]=[C:19]([CH3:18])[CH:20]=[CH:21][C:22]=1[C:2]1[CH:11]=[C:10]([CH:12]([OH:17])[C:13]([F:16])([F:15])[F:14])[CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=1)#[N:25]

Participants

7

Reactant 2

HCID 58188392Methyl 3-bromo-5-(2,2,2-trifluoro-1-hydroxyethyl)benzoateHCID 584073295-Methyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Product 1

HCID 58188274Methyl 2'-cyano-4'-methyl-5-(2,2,2-trifluoro-1-hydroxyethyl)biphenyl-3-carboxylate

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 3-bromo-5-(2,2,2-trifluoro-1-hydroxyethyl)benzoate (300 mg, 0.96 mmol), 5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (280 mg, 1.1 mmol), tetrakis(triphenylphosphine)palladium(0) (60 mg, 0.052 mmol) in N,N-dimethylformamide (0.75 mL) and toluene (1.5 mL) under nitrogen was subjected to microwave irradiation at 110° C. for 1 h. After cooling, the mixture was diluted with water (15 mL) and extracted with EtOAc (20 mL×3). The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated. The residue was purified by flash chromatography to afford the title compound.

Workup

  1. customirradiation at 110° C. for 1 h
  2. temperatureAfter cooling
  3. extractionextracted with EtOAc (20 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-dc6818cd730941c9b05f985ae6ff2935
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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