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

HRID 579369
ノート
印刷プレビュー

反応式

HRID 579369 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 178517115HCID 178517115、化合物

生成物 1

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

試薬・触媒・溶媒 3

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

反応条件

温度
90 °C

実験手順

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+].)

後処理

  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)

出典と根拠

ORDレコード
ord-c2fb867fa4204514aa22184a3c521273
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09040712B2

反応ノート

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