Sodium Chloride → 3-[6-Methyl-4-(4-trifluoromethyl-phenyl)pyridin-2-yl]-benzeneboronic acid

HRID 1989253Notes

Reaction equation

HRID 1989253 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[CH:11]=[C:10]([CH3:24])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[B:25](OC(C)C)([O:30]C(C)C)[O:26]C(C)C.[Li]CCCC.[Na+].[Cl-]>C1COCC1>[CH3:24][C:10]1[N:9]=[C:8]([C:4]2[CH:3]=[C:2]([B:25]([OH:30])[OH:26])[CH:7]=[CH:6][CH:5]=2)[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH:11]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 21531Triisopropyl borate2×HCID 574687452-(3-Bromo-phenyl)-6-methyl-4-(4-trifluoromethyl-phenyl)-pyridineHCID 178418339Butyllithium2×

Product 1

HCID 602093413-[6-Methyl-4-(4-trifluoromethyl-phenyl)pyridin-2-yl]-benzeneboronic acidYield 120.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-bromo-phenyl)-6-methyl-4-(4-trifluoromethyl-phenyl)-pyridine (example E.21) (4.00 g, 10.2 mmol) and triisopropyl borate (2.23 g, 11.8 mmol) in THF (60 mL) at −78° C. was added n-BuLi (1.6 M in hexane, 6.50 mL, 10.4 mmol) keeping the internal temperature below −65° C. Stirring was continued at −78° C. for 45 min, again triisopropyl borate (1.11 g, 5.9 mmol) and n-BuLi (1.6 M in hexane, 3.25 mL, 5.2 mmol) were added and stirring was continued at −78° C. for 30 min. A 1 M aqueous solution of NaH2PO4.2H2O was added, saturated with solid NaCl and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and the solvent was removed in vacuum to give the title compound as a yellow solid (4.39 g, 96%). MS (ISP) 358.2 [(M+H)+]; mp 140° C. (dec.).

Workup

  1. customthe internal temperature below −65° C
  2. stirringstirring
  3. waitwas continued at −78° C. for 30 min
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuum

Sources & evidence

ORD record
ord-095cc0c90d2a487abf2eabeb12a1b55e
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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