6-Bromo-3,5-dimethoxypicolinonitrile → 6-Ethyl-3,5-dimethoxy-pyridine-2-carbonitrile

HRID 76097

反応式

HRID 76097 の反応式
Br[C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[O:12][CH3:13].[CH2:14]([Mg]Br)[CH3:15]>O1CCCC1.[Ni](Cl)Cl.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:14]([C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([O:10][CH3:11])=[CH:4][C:3]=1[O:12][CH3:13])[CH3:15]

参加物

5

反応物 2

HCID 735549116-Bromo-3,5-dimethoxypicolinonitrileHCID 178418443HCID 178418443、化合物

生成物 1

HCID 669867776-Ethyl-3,5-dimethoxy-pyridine-2-carbonitrile

試薬・触媒・溶媒 2

HCID 2724937Dichloro(1,1'-(1,3-propanediyl)bis(1,1-diphenylphosphine-kappaP))nickel触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Impure 6-bromo-3,5-dimethoxy-pyridine-2-carbonitrile (462 mg; <1.9 mmol) was dissolved in tetrahydrofuran (20 mL) under nitrogen, and to the solution was added 1,3-bis(diphenylphosphino)propane nickel (II) chloride (105 mg; 0.19 mmol). The solution was cooled to 0° C., and a solution of ethyl magnesium bromide (1.0 molar in THF; 2.7 mL; 1.4 eq.) was slowly added. The reaction was stirred for five minutes, and quenched with saturated aqueous ammonium chloride (10 mL). To the reaction was added ethyl acetate (40 mL) and water (40 mL). The organic layer was isolated, dried over sodium sulfate, evaporated, and purified by column chromatography to give 6-ethyl-3,5-dimethoxy-pyridine-2-carbonitrile (114 mg; 0.6 mmol).

後処理

  1. customquenched with saturated aqueous ammonium chloride (10 mL)
  2. additionTo the reaction was added ethyl acetate (40 mL) and water (40 mL)
  3. customThe organic layer was isolated
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. custompurified by column chromatography

出典と根拠

ORDレコード
ord-532f1d6b6fa349359073f09aec098b3b
出典データセット
uspto-grants-2014_09
特許番号
US08835464B2

関連ノート

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