Triisopropyl borate → 5-Methylpyridine-3-boronic acid

HRID 2427515Notes

Reaction equation

HRID 2427515 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[N:6][CH:7]=1.C([Li])CCC.[B:14](OC(C)C)([O:19]C(C)C)[O:15]C(C)C>CCOCC>[CH3:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([B:14]([OH:19])[OH:15])[CH:3]=1

Participants

5

Reactant 3

HCID 21531Triisopropyl borateHCID 8177133-Bromo-5-methylpyridineHCID 178418339Butyllithium

Product 1

HCID 27627085-Methylpyridine-3-boronic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 5-bromo-3-picoline (0.25 g, 1.45 mmol) in Et2O (5 mL) at −78° C., was added n-butyl lithium (1.6 M in hexanes, 0.92 mL, 1.48 mmol) dropwise. The mixture was stirred at −78° C. for 1 hour and then triisopropyl borate was added quickly. The mixture was stirred at −78° C. for 1 hour and then quenched with water (2 mL). The mixture was warmed up to room temperature overnight. Solvent was removed under reduced pressure to yield a yellow solid (0.25 g).

Workup

  1. stirringThe mixture was stirred at −78° C. for 1 hour
  2. customquenched with water (2 mL)
  3. temperatureThe mixture was warmed up to room temperature overnight
  4. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-52b7067e65404406b2f7aca1190a79d6
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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