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

HRID 1643176ノート

反応式

HRID 1643176 の反応式
[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

参加物

4

反応物 2

HCID 5550542-Bromo-3-nitropyridineHCID 178418507HCID 178418507、化合物

生成物 1

HCID 196964567-Bromo-6-azaindole収率 60%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-fb270304bbbf4a7eb9857822f77325c5
出典データセット
uspto-grants-2012_02
特許番号
US08119683B2

反応ノート

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