Tributyl(prop-1-yn-1-yl)stannane → 2-(3-(3-(Prop-1-YN-1-YL)pyrazin-2-YL)azetidin-1-YL)quinoline

HRID 1850341노트

반응식

HRID 1850341 반응식
Cl[C:2]1[C:3]([CH:8]2[CH2:11][N:10]([C:12]3[CH:21]=[CH:20][C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=3)[CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.[CH2:22]([Sn](CCCC)(CCCC)C#CC)[CH2:23][CH2:24]C>O1CCOCC1.[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[C:22]([C:2]1[C:3]([CH:8]2[CH2:11][N:10]([C:12]3[CH:21]=[CH:20][C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=3)[CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1)#[C:23][CH3:24]

참가 물질

5

반응물 2

HCID 2733165Tributyl(prop-1-yn-1-yl)stannaneHCID 585467412-(3-(3-Chloropyrazin-2-yl)azetidin-1-yl)quinoline

생성물 1

HCID 585474572-(3-(3-(Prop-1-YN-1-YL)pyrazin-2-YL)azetidin-1-YL)quinoline수율 68%

시약·촉매·용매 2

HCID 2734558Bis(tri-tert-butylphosphine)palladium(0)촉매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

A mixture of 2-(3-(3-chloropyrazin-2-yl)azetidin-1-yl)quinoline (0.200 g, 0.674 mmol), tributyl(prop-1-yn-1-yl)stannane (0.266 g, 0.809 mmol), and bis(tri-t-butylphosphine) palladium (o) (0.017 g, 0.034 mmol) in p-dioxane (4 mL) was heated at 100° C. in 16 h. The reaction mixture was cooled, concentrated, and purified by ISCO (0-60% EtOAc/Hexanes) to give the title compound (128 mg, 68%).

후처리

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. custompurified by ISCO (0-60% EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-92afb8d204ea48419b5480b067ddbcff
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957073B2

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