Trimethyl borate → Quinoline-3-boronic acid

HRID 1780313Notes

Reaction equation

HRID 1780313 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C([Li])(C)(C)C.[B:17](OC)([O:20]C)[O:18]C>C1COCC1>[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[C:2]([B:17]([OH:20])[OH:18])[CH:3]=1

Participants

5

Reactant 3

HCID 8470Trimethyl borateHCID 214133-BromoquinolineHCID 178418306HCID 178418306, compound

Product 1

HCID 2734663Quinoline-3-boronic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

3-Bromoquinoline (0.4 mL, 3 mmol) was dissolved in THF, and the solution was cooled to -78° C. To this solution was added t-butyllithium (4.1 mL, 7 mmol), and the reaction mixture was stirred for 20 minutes. Trimethyl borate (0.81 mL, 7.1 mmol) was added at -78° C., and the mixture was stirred and allowed to warm to room temperature. The reaction was quenched with water, and the solvents were removed under vacuum. The residue 180 mg was taken directly to the next step.

Workup

  1. stirringthe mixture was stirred
  2. temperatureto warm to room temperature
  3. customThe reaction was quenched with water
  4. customthe solvents were removed under vacuum

Sources & evidence

ORD record
ord-e42e0d5b594a410eae4e106e1e32ed9e
Source dataset
uspto-grants-1997_05
Patent number
US05629325

Reaction notes

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