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

HRID 470567ノート

反応式

HRID 470567 の反応式
[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

参加物

7

反応物 5

HCID 14742,2'-BipyridineHCID 10340Sodium Carbonate2 回HCID 25517Ammonium ChlorideHCID 8171154-Bromo-2-hydroxypyridineHCID 2760897Cyclopropylboronic acid2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-8c3a072179f8406dafb2c4af0f4f3871
出典データセット
uspto-grants-2014_01
特許番号
US08629138B2

反応ノート

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