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

HRID 76097

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HRID 76097 반응식
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]

참가 물질

5

반응물 2

HCID 735549116-Bromo-3,5-dimethoxypicolinonitrileHCID 178418443HCID 178418443, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 2724937Dichloro(1,1'-(1,3-propanediyl)bis(1,1-diphenylphosphine-kappaP))nickel촉매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-532f1d6b6fa349359073f09aec098b3b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835464B2

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