Potassium Carbonate → Phenylboronic Acid

HRID 404968Notes

Reaction equation

HRID 404968 reaction equation
C(=O)([O-])[O-].[K+].[K+].C1(N2CCC3C(=CC(O)=CC=3)C2=O)CCCC1.BrC[C:26]1[CH:27]=[C:28]([B:32]([OH:34])[OH:33])[CH:29]=[CH:30][CH:31]=1>CC(C)=O>[C:28]1([B:32]([OH:34])[OH:33])[CH:29]=[CH:30][CH:31]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27732813-(Bromomethyl)benzeneboronic acidHCID 66799500HCID 66799500, compound

Product 1

HCID 66827Phenylboronic AcidYield 215.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (0.166 g, 1.2 mmol) was added to a solution of 2-cyclopentyl-7-hydroxy-3,4-dihydroisoquinolin-1(2H)-one (0.235 g, 1 mmol) and 3-(bromomethyl)phenylboronic acid (0.257 g, 1.2 mmol) in acetone (10 mL). After stirring for 1 h at 60° C., the reaction mixture was cooled to room temperature and filtered and the filtrate was evaporated under reduced pressure to give crude 34(2-cyclopentyl-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yloxy)methyl)phenylboronic acid as a colorless solid (0.315 g, 85%). The crude product was used for the next step without further purification. 1H NMR (400 MHz, DMSO-d6): δ 8.12 (s, 2H), 7.83 (s, 1H), 7.73-7.68 (m, 2H), 7.56 (s, 1H), 7.47 (d, 1H, J=7.8 Hz), 7.32 (t, 1H, J=7.8 Hz), 7.04 (d, 1H, J=8.7 Hz), 5.25 (s, 2H), 4.85-4.81 (m, 1H), 2.01-1.98 (m, 2H), 1.75-1.59 (m, 6H). LC-MS (ESI) Calcd for C19H20BNO4S [M+H]+: 370.12. Found: 369.90.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8e293035f5924e80b61a9b7a87a02c33
Source dataset
uspto-grants-2014_06
Patent number
US08748632B2

Reaction notes

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