Trimethyl borate → Quinoline-3-boronic acid

HRID 2305100Notes

Reaction equation

HRID 2305100 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-387a7315e00647e4b642e8ed67ebf502
Source dataset
uspto-grants-2002_08
Patent number
US06437138B1

Reaction notes

Loading…