Trimethyl borate → HCID 86727191, compound

HRID 579367Notes

Reaction equation

HRID 579367 reaction equation
Br[C:2]1[C:3](=[O:15])[N:4]([CH3:14])[C:5]2[C:10]([C:11]=1[O:12][CH3:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.C([Li])CCC.[B:21](OC)([O:24]C)[O:22]C>C1COCC1.Cl>[CH3:13][O:12][C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH3:14])[C:3](=[O:15])[C:2]=1[B:21]([OH:24])[OH:22]

Participants

6

Reactant 3

HCID 8470Trimethyl borateHCID 86137547HCID 86137547, compoundHCID 178418339Butyllithium

Product 1

HCID 86727191HCID 86727191, compoundYield 63.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-4-methoxy-1-methylquinolin-2(1H)-one (2.7 g, 10.07 mmol) in THF (5 mL) was added n-butyllithium (2.5 M in Hexane, 4.03 mL) under nitrogen atmosphere at −78° C. and the reaction mixture was maintained at this temperature for 1 h. A cooled solution of trimethyl borate (1.35 mL, 12.08 mmol) was added at −78° C., and the reaction mixture was maintained at this temperature for 2 h. The reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was diluted with 1M HCl and a white solid precipitated from the solution. The precipitate was filtered, washed with water and EtOAc, then dried under high vacuum to provide (4-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)boronic acid (1.5 g, MS: 234.1 [M+H+].)

Workup

  1. temperaturethe reaction mixture was maintained at this temperature for 1 h
  2. temperaturethe reaction mixture was maintained at this temperature for 2 h
  3. customa white solid precipitated from the solution
  4. filtrationThe precipitate was filtered
  5. washwashed with water and EtOAc
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-fa0ce2bba56f41f6a20f7011af94ced9
Source dataset
uspto-grants-2015_05
Patent number
US09040712B2

Reaction notes

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