2-Chloro-3-nitropyridine → 7-Chloro-1H-pyrrolo[2,3-c]pyridine

HRID 20206

반응식

HRID 20206 반응식
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH:11]([Mg]Br)=[CH2:12]>C1COCC1>[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:7]=1[NH:8][CH:12]=[CH:11]2

참가 물질

4

반응물 2

HCID 796132-Chloro-3-nitropyridineHCID 178418507HCID 178418507, 화합물

생성물 1

HCID 114350487-Chloro-1H-pyrrolo[2,3-c]pyridine수율 31%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

2-Chloro-3-nitropyridine 22e (5.0 g) was dissolved in dry THF (200 ml). After the solution was cooled down to −78° C., an excess of vinyl magnesium bromide (1.0 M in THF, 100 ml) was added. Then, the reaction was left at −20° C. for eight hours before being quenched with 20% NH4Cl (150 ml). The aqueous phase was extracted with EtOAc (3×150 ml). The combined organic layer was dried over MgSO4. After filtration and concentration, the crude product was purified by silica gel column chromatography to afford 1.5 g of 7-chloro-6-azaindole 1e in 31% yield.

후처리

  1. custombefore being quenched with 20% NH4Cl (150 ml)
  2. extractionThe aqueous phase was extracted with EtOAc (3×150 ml)
  3. dry with materialThe combined organic layer was dried over MgSO4
  4. filtrationAfter filtration and concentration
  5. customthe crude product was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-ad0ffa5f287d47419e66a71ebd0496d1
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745625B2

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