Potassium Acetate → 5-Methyl-1-oxo-1,2-dihydro-isoquinoline-3-boronic acid

HRID 717110Notes

Reaction equation

HRID 717110 reaction equation
Cl[C:2]1[NH:3][C:4](=[O:13])[C:5]2[C:10]([CH:11]=1)=[C:9]([CH3:12])[CH:8]=[CH:7][CH:6]=2.[B:14]1(B2OC(C)(C)C(C)(C)O2)[O:18]C(C)(C)C(C)(C)[O:15]1.CC([O-])=O.[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:12][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:11]=[C:2]([B:14]([OH:18])[OH:15])[NH:3][C:4]2=[O:13]

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 229310333-Chloro-5-methyl-2H-isoquinolin-1-one

Product 1

HCID 898128145-Methyl-1-oxo-1,2-dihydro-isoquinoline-3-boronic acidYield 49%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

3-Chloro-5-methyl-2H-isoquinolin-1-one (100 mg, 0.52 mmol), bis(pinacolato)diboron (157 mg, 0.62 mmol), Pd(dppf)Cl2 (42 mg, 0.054 mmol) and KOAc (153 mg, 1.56 mmol) in 1,4-dioxane (2 mL) were added to a microwave vial and the reaction mixture purged with N2 for 10 min. The reaction mixture was irradiated using a microwave reactor (300 W, 120° C., 20 min). The reaction mixture was passed through a Si-thiol cartridge and concentrated in vacuo. The crude product was purified by reverse phase preparative HPLC-MS to afford 5-methyl-1-oxo-1,2-dihydro-isoquinoline-3-boronic acid as a white solid (51 mg, 49%).

Workup

  1. customthe reaction mixture purged with N2 for 10 min
  2. customThe reaction mixture was irradiated
  3. custom(300 W, 120° C., 20 min)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by reverse phase preparative HPLC-MS

Sources & evidence

ORD record
ord-b3be7816c3b24018a8ae8c5ab7e4c3e8
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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