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

HRID 46330

反応式

HRID 46330 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-6274da3e6fdd4badbbf2fa3c0e80ad14
出典データセット
uspto-grants-2013_09
特許番号
US08541588B2

関連ノート

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