Triisopropyl borate → HCID 60209342, compound

HRID 1927977Notes

Reaction equation

HRID 1927977 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[Li]CCCC.[B:30](OC(C)C)([O:35]C(C)C)[O:31]C(C)C>CC(OC)(C)C>[CH3:14][C:12]1[CH:11]=[C:10]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[N:9]=[C:8]([C:4]2[CH:3]=[C:2]([B:30]([OH:35])[OH:31])[CH:7]=[CH:6][CH:5]=2)[CH:13]=1

Participants

5

Reactant 3

HCID 21531Triisopropyl borateHCID 57468804HCID 57468804, compoundHCID 178418339Butyllithium

Product 1

HCID 60209342HCID 60209342, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(3-bromo-phenyl)-4-methyl-6-(4-trifluoromethyl-phenyl)-pyridine (example E.90) (1.23 g, 3.13 mmol) in TBME (80 mL) at −78° C. was added n-BuLi (1.6 M in hexane, 3.2 mL, 5.0 mmol) keeping the internal temperature below −60° C. (ca. 3 min), stirring was continued at −78° C. for 25 min, then triisopropyl borate (1.5 mL, 6.27 mmol) was added quickly, causing the internal temperature to rise to −60° C., stirring was continued at −78° C. for 20 min. The mixture was quenched by addition of 1M NaH2PO4.2H2O-solution, the cooling bath was removed and the mixture was allowed to warm to 0° C. and stirred at 0° C. for 10 min. Diluted with EtOAc and brine, extracted three times with EtOAc, dried the combined organic layers over Na2SO4. Removal of the solvent in vacuum left the title compound as a light brown foam (1.20 g, 70.5%, purity: 65.8%), which was used without further purification. MS (ISP) 358.2 [(M+H)+].

Workup

  1. customthe internal temperature below −60° C. (ca. 3 min)
  2. customto rise to −60° C.
  3. stirringstirring
  4. waitwas continued at −78° C. for 20 min
  5. customThe mixture was quenched by addition of 1M NaH2PO4.2H2O-solution
  6. customthe cooling bath was removed
  7. stirringstirred at 0° C. for 10 min
  8. additionDiluted with EtOAc and brine
  9. extractionextracted three times with EtOAc
  10. dry with materialdried the combined organic layers over Na2SO4
  11. customRemoval of the solvent in vacuum
  12. waitleft the title compound as a light brown foam (1.20 g, 70.5%, purity: 65.8%), which
  13. customwas used without further purification

Sources & evidence

ORD record
ord-f39ba06078a04038a55cf0b0fc66a2d7
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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