Hydrochloric Acid → Quinoxalin-6-ylboronic acid

HRID 571447Notes

Reaction equation

HRID 571447 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([B:11]3[O:19]C(C)(C)C(C)(C)[O:12]3)=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1.O.Cl.CCOC(C)=O>C1COCC1>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([B:11]([OH:19])[OH:12])=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 441182986-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline

Product 1

HCID 45073596Quinoxalin-6-ylboronic acidYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To 6-quinoxaline boronic acid pinacol ester (S50) (256 mg, 1.00 mmol, 1.00 equiv) in THF (2.0 mL) at 23° C. was added H2O (8.0 mL) and NaIO4 (321 mg, 1.50 mmol, 1.50 equiv). After stirring for 1.0 hr at 23° C., the reaction mixture was added to 1N HCl aq (20 mL) and was further stirred for 1.0 hr. To the reaction mixture was added EtOAc (20 mL) and the phases were separated. The aqueous phase was extracted with EtOAc (2×20 mL). The combined organic phases are washed with brine (20 mL) and dried (Na2SO4). The filtrate was concentrated in vacuo and the residue was triturated with Et2O to afford 121 mg of the title compound as a colorless solid (70% yield).

Workup

  1. stirringwas further stirred for 1.0 hr
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted with EtOAc (2×20 mL)
  4. washThe combined organic phases are washed with brine (20 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was triturated with Et2O

Sources & evidence

ORD record
ord-f8c6885228864c989c953c677f519d3e
Source dataset
uspto-grants-2015_05
Patent number
US09024093B2

Reaction notes

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