2,2'-Bipyridine → 4-Bromo-1-cyclopropylpyridin-2(1H)-one

HRID 406778노트

반응식

HRID 406778 반응식
[Br:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.[CH:9]1(B(O)O)[CH2:11][CH2:10]1.N1C=CC=CC=1C1C=CC=CN=1.C([O-])([O-])=O.[Na+].[Na+].[NH4+].[Cl-]>ClCCCl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]([CH:9]2[CH2:11][CH2:10]2)[C:4](=[O:8])[CH:3]=1

참가 물질

7

반응물 5

HCID 14742,2'-BipyridineHCID 10340Sodium Carbonate2회HCID 25517Ammonium ChlorideHCID 8171154-Bromo-2-hydroxypyridineHCID 2760897Cyclopropylboronic acid2회

생성물 1

HCID 596356474-Bromo-1-cyclopropylpyridin-2(1H)-one

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

A flask charged with a stir bar, 4-bromo-1H-pyridin-2-one (1.80 g), cyclopropylboronic acid (2.00 g), Cu(O2CCH3)2 (2.00 g), 2,2′-bipyridine (1.70 g), Na2CO3 (2.47 g), and 1,2-dichloroethane (75 mL) was heated to 70° C. The mixture was stirred at this temperature in air overnight. Then, further portions of cyclopropylboronic acid (0.50 g) and Na2CO3 (0.55 g) were added and the mixture was stirred at reflux temperature for another 4 h. After cooling to ambient temperature, aqueous NH4Cl solution was added and the resultant mixture was extracted with dichloromethane. The combined organic extracts were dried (MgSO4) and the solvent was evaporated. The residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate 50:50→35:65) to afford the title compound as an oil that crystallized on standing. Yield: 0.82 g (37% of theory); Mass spectrum (ESI+): m/z=214/216 (Br) [M+H]+.

후처리

  1. additionA flask charged with a stir bar
  2. stirringthe mixture was stirred
  3. temperatureat reflux temperature for another 4 h
  4. extractionthe resultant mixture was extracted with dichloromethane
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. customthe solvent was evaporated
  7. customThe residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate 50:50→35:65)

출처 및 근거

ORD 기록
ord-ceb7b568da4c4ad7bf74a243f78bc627
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754076B2

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