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2,2'-Bipyridine → 1-cyclopropyl-4-iodopyridin-2(1H)-one

HRID 406759
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HRID 406759 반응식
[I:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.C1C=CN=C(C2C=[CH:17][CH:18]=[CH:19]N=2)C=1.C1(B(O)O)CC1.C([O-])([O-])=O.[Na+].[Na+]>ClC(Cl)C.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH:17]1([N:5]2[CH:6]=[CH:7][C:2]([I:1])=[CH:3][C:4]2=[O:8])[CH2:18][CH2:19]1
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참가 물질

7

반응물 4

HCID 14742,2'-BipyridineHCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 205825354-Iodo-1,2-dihydropyridin-2-one

생성물 1

HCID 591903761-cyclopropyl-4-iodopyridin-2(1H)-one수율 81%

시약·촉매·용매 2

HCID 8895Cupric acetate
촉매
HCID 63651,1-Dichloroethane용매

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온도
70 °C

실험 절차

A mixture of 4-iodopyridin-2(1H)-one (0.2425 g, 1.10 mmol, 1.0 equiv), Cu(OAc)2 (0.2146 g, 1.18 mmol, 1.07 equiv), bipyridine (0.1832 g, 1.17 mmol, 1.07 equiv), cyclopropylboronic acid (0.2122 g, 2.47 mmol, 2.25 equiv) and Na2CO3 (0.2638 g, 2.49 mmol, 2.27 equiv) in dichloroethane (10 mL) was stirred at 70° C. for 18 h. The reaction mixture was quenched with satd aq NH4Cl, diluted with CH2Cl2, and dried over Na2SO4. After the solvent was removed under reduced pressure, the residue was purified by chromatography on silica gel eluted with hexanes/ethyl acetate to afford 0.2309 g (81%) of 1-cyclopropyl-4-iodopyridin-2(1H)-one. Step 2

후처리

  1. customThe reaction mixture was quenched with satd aq NH4Cl
  2. additiondiluted with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. customAfter the solvent was removed under reduced pressure
  5. customthe residue was purified by chromatography on silica gel
  6. washeluted with hexanes/ethyl acetate

출처 및 근거

ORD 기록
ord-71d90882133443c3a4a4ee28803786c2
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08754076B2

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