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

HRID 2277718노트

반응식

HRID 2277718 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-3a2bd08742fa410281012d5d0d629ce5
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133158B2

반응 노트

불러오는 중…