3,5-Dibromopyridine → Tert-butyl 4-(5-bromopyridin-3-yl)piperazine-1-carboxylate

HRID 2277718ノート

反応式

HRID 2277718 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19](Br)[CH:20]=1.CC(C)([O-])C.[Na+]>O1CCOCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:19]2[CH:18]=[N:17][CH:16]=[C:15]([Br:14])[CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 3

HCID 693693,5-DibromopyridineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 23676156Sodium t-butoxide

生成物 1

HCID 11653049Tert-butyl 4-(5-bromopyridin-3-yl)piperazine-1-carboxylate収率 54%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of piperazine-1-carboxylic acid tert-butyl ester (1.86 g, 10 mmol), 3,5-dibromopyridine (2.37 g, 10 mmol), palladium(II) acetate (0.11 g, 0.5 mmol), anphos (0.35 g, 0.6 mmol), and sodium tert-butoxide (1.68 g, 15 mmol) in dioxane (10 mL) was heated at 130° C. in a microwave reactor for 2 hours. The mixture was then diluted with water, and extracted with EtOAc. The organic layer was dried over anhy. Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (eluent with ethyl acetate:hexane=1:5) to afford the title compound as a white solid (1.84 g, 54%). MS: 342.2 (M+).

後処理

  1. extractionextracted with EtOAc
  2. customThe organic layer was dried over anhy
  3. filtrationNa2SO4, filtered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (eluent with ethyl acetate:hexane=1:5)

出典と根拠

ORDレコード
ord-3a2bd08742fa410281012d5d0d629ce5
出典データセット
uspto-grants-2015_09
特許番号
US09133158B2

反応ノート

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