3-Nitropyridine → 6-Azaindole

HRID 392132

반응식

HRID 392132 반응식
[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

참가 물질

4

반응물 2

HCID 1376303-NitropyridineHCID 178418507HCID 178418507, 화합물

생성물 1

HCID 92196-Azaindole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-20 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-74628ef804be4d30a069d0b6e8947871
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06800640B2

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