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

HRID 579369
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HRID 579369 반응식
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
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참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

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

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온도
90 °C

실험 절차

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+].)

후처리

  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)

출처 및 근거

ORD 기록
ord-c2fb867fa4204514aa22184a3c521273
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09040712B2

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