2-Bromo-3-nitropyridine → 7-Bromo-6-azaindole

HRID 1643176노트

반응식

HRID 1643176 반응식
[Br: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>[Br: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 5550542-Bromo-3-nitropyridineHCID 178418507HCID 178418507, 화합물

생성물 1

HCID 196964567-Bromo-6-azaindole수율 60%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2-Bromo-3-nitropyridine (1 in Scheme 1, 2.0 g, 98%, 9.7 mmol) in dry THF (80 mL) was cooled to −78° C. Excess vinylmagnesium bromide (1.0 M in THF, 40 mL, 40 mmol) was added. The reaction mixture was stirred at −40˜−50° C. for 1 h before it was quenched with saturated NaHCO3 solution. The layers were separated and the aqueous layer was extracted with EtOAc (3 times). The combined organic layers were dried over MgSO4, the dried solution was filtered, and the filtrate was concentrated. The residue was purified by flash chromatography (EtOAc:n-hexane=1:2) to afford 2 (1.1 g, 60%).

후처리

  1. customwas quenched with saturated NaHCO3 solution
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc (3 times)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationthe dried solution was filtered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by flash chromatography (EtOAc:n-hexane=1:2)

출처 및 근거

ORD 기록
ord-fb270304bbbf4a7eb9857822f77325c5
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119683B2

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