Methanol → (2-Methoxyquinolin-3-yl)boronic acid

HRID 251744Notes

Reaction equation

HRID 251744 reaction equation
F[C:2]1[C:11]([B:12]([OH:14])[OH:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:15][OH:16]>Cl>[CH3:15][O:16][C:2]1[C:11]([B:12]([OH:14])[OH:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 27832712-Fluoroquinoline-3-boronic acid

Product 1

HCID 16106577(2-Methoxyquinolin-3-yl)boronic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(2-Fluoroquinolin-3-yl)boronic acid was dissolved in 1.25M HCl in MeOH and stirred for 1 hr at RT. The mixture was quenched with sat. aq. NaHCO3 solution and the mixture was extracted with DCM (3×). The organics were dried (Na2SO4) and concentrated under reduced pressure to yield the crude product as a pale yellow solid which was used in the next step without further purification. MS (ES) C10H10BNO3 requires: 203, found: 204 (M+H)+.

Workup

  1. customThe mixture was quenched with sat. aq. NaHCO3 solution
  2. extractionthe mixture was extracted with DCM (3×)
  3. dry with materialThe organics were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8a26d1a04c394fd5ac2292506edfe276
Source dataset
uspto-grants-2011_01
Patent number
US07863294B2

Reaction notes

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