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Dichloromethane → (2-Oxo-1,2-dihydroquinolin-3-yl)boronic acid

HRID 579369
Notes
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Reaction equation

HRID 579369 reaction equation
Br[C:2]1[C:3]([OH:12])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[B:13]1(B2OC(C)(C)C(C)(C)O2)[O:17]C(C)(C)C(C)(C)[O:14]1.C([O-])(=O)C.[K+].C(Cl)Cl>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].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.[Fe+2].O1CCOCC1>[O:12]=[C:3]1[C:2]([B:13]([OH:17])[OH:14])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 178517115HCID 178517115, compound

Product 1

HCID 49757966(2-Oxo-1,2-dihydroquinolin-3-yl)boronic acidYield 71.2%

Reagents, catalysts & solvents 3

HCID 635956
Ferrocene-1,1'-bis-(diphenylphosphine)
Catalyst
HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a microwave vial was added 3-bromo-2-hydroxyquinoline (50 mg, 0.223 mmol), bis(pinacolato)diboron (113 mg, 0.446 mmol), potassium acetate (66 mg, 0.669 mmol), PdCl2(dppf). CH2Cl2 (18.22 mg, 0.022 mmol), and dppf (12.37 mg, 0.022 mmol), followed by addition of 1,4-dioxane (6 mL). The reaction mixture was purged with N2 and stirred under N2 atmosphere at 90° C. overnight. The reaction mixture was filtered through a disposable filter funnel, concentrated in vacuo, and purified by silica gel chromotography (10% to 60% EtOAc in heptane) to afford (2-oxo-1,2-dihydroquinolin-3-yl)boronic acid (30 mg, MS: 190.1 [M+H+].)

Workup

  1. customThe reaction mixture was purged with N2
  2. filtrationThe reaction mixture was filtered through a disposable filter funnel
  3. concentrationconcentrated in vacuo
  4. custompurified by silica gel chromotography (10% to 60% EtOAc in heptane)

Sources & evidence

ORD record
ord-c2fb867fa4204514aa22184a3c521273
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09040712B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes