Hydrochloric Acid → 4-(5-Chloro-2-hydroxyphenyl)pyridine-2-carbonitrile

HRID 46330

반응식

HRID 46330 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6](B(O)O)[CH:7]=1.Cl[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([C:19]#[N:20])[CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl>O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([C:19]#[N:20])[CH:14]=2)[CH:7]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 6933424-Chloro-2-pyridinecarbonitrileHCID 23005362(5-Chloro-2-hydroxyphenyl)boronic Acid (contains varying amounts of Anhydride)

생성물 1

HCID 1360636254-(5-Chloro-2-hydroxyphenyl)pyridine-2-carbonitrile수율 8.6%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

(5-Chloro-2-hydroxyphenyl)boronic acid (2.0 g, 0.012 mol), 4-chloropyridine-2-carbonitrile (1.61 g, 0.012 mol), (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II) (0.424 g, 0.00058 mol) and sodium carbonate (3.7 g, 0.035 mol) in 1,4-dioxane (20.0 mL) and deionised water (1.0 mL) were degassed with nitrogen (×3) before heating at 100° C. for 18 hours under nitrogen. The reaction was cooled and hydrochloric acid (2.0 M aqueous solution, 30.0 mL) added. Reaction was filtered, washing with ethyl acetate (50.0 mL). The organic layer was concentrated in vacuo and purified by flash column chromatography on the ISCO™ (40 g SiO2) eluting with ethyl acetate:heptane (gradient 0:1 to 7:3, by volume) to afford the title compound as a yellow solid, 0.23 g, 8.6% yield.

후처리

  1. temperatureThe reaction was cooled
  2. customReaction
  3. filtrationwas filtered
  4. washwashing with ethyl acetate (50.0 mL)
  5. concentrationThe organic layer was concentrated in vacuo
  6. custompurified by flash column chromatography on the ISCO™ (40 g SiO2)
  7. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-6274da3e6fdd4badbbf2fa3c0e80ad14
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541588B2

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