3-Nitropyridine → 6-Azaindole

HRID 731600

反応式

HRID 731600 の反応式
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.[CH:10]([Mg]Br)=[CH2:11]>C1COCC1>[NH:1]1[C:4]2[C:9](=[CH:8][CH:7]=[N:6][CH:5]=2)[CH:11]=[CH:10]1

参加物

4

反応物 2

HCID 1376303-NitropyridineHCID 178418507HCID 178418507、化合物

生成物 1

HCID 92196-Azaindole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

A solution of 3-nitropyridine in THF at −78° C. is treated with vinyl magnesium bromide (3 eq), stirred at −20° C. for 8 h and quenched with 20% ammonium chloride. The phases are separated and the aqueous phase is extracted with EtOAc. The organic phase and the combined extracts are mixed together, dried over MgSO4 and concentrated in vacuo. The resultant residue is chromatographed over silica gel to afford the title 6-azaindole.

後処理

  1. customquenched with 20% ammonium chloride
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted with EtOAc
  4. additionThe organic phase and the combined extracts are mixed together
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue is chromatographed over silica gel

出典と根拠

ORDレコード
ord-bb8cadeaf8024cf5b1bfb40dd98c6bc1
出典データセット
uspto-grants-2009_09
特許番号
US07585876B2

関連ノート

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