5-Bromo-3-nitropyridine-2-carbonitrile → 5-(3-Methyl(2-pyridyl))-3-nitropyridine-2-carbonitrile

HRID 1791269ノート

反応式

HRID 1791269 の反応式
Br[C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[Br-].[CH3:14][C:15]1[C:16]([Zn+])=[N:17][CH:18]=[CH:19][CH:20]=1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:14][C:15]1[C:16]([C:2]2[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([C:8]#[N:9])=[N:6][CH:7]=2)=[N:17][CH:18]=[CH:19][CH:20]=1

参加物

5

反応物 2

HCID 27696985-Bromo-3-nitropyridine-2-carbonitrileHCID 178426320HCID 178426320、化合物

生成物 1

HCID 220302915-(3-Methyl(2-pyridyl))-3-nitropyridine-2-carbonitrile収率 88%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

Heat a solution of 5-bromo-3-nitropyridine-2-carbonitrile (228 mg, 1.0 mmol), tetrakis(triphenylphosphine)palladium(0) (15 mg), 3-methyl-2-pyridylzinc bromide (0.5 M in THF, 3 mL, 1.5 mmol) in THF (5 mL) at 60° C. for 2 hours. Cool the solution and partition between ethyl acetate (10 mL) and saturated aqueous NaHCO3 (10 mL). Extract the aqueous layer with ethyl acetate (2×15 mL), wash with water (10 mL) and brine (10 mL), dry (MgSO4) and evaporate to give the title compound as a pale yellow solid (211 mg, 88%).

後処理

  1. temperatureCool the solution
  2. custompartition between ethyl acetate (10 mL) and saturated aqueous NaHCO3 (10 mL)
  3. extractionExtract the aqueous layer with ethyl acetate (2×15 mL)
  4. washwash with water (10 mL) and brine (10 mL)
  5. dry with materialdry (MgSO4)
  6. customevaporate

出典と根拠

ORDレコード
ord-5b19e67aa6484aacaa880438d505242b
出典データセット
uspto-grants-2006_07
特許番号
US07074799B2

反応ノート

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