Cesium carbonate → 5-Nitro-2,3'-bipyridin-6-amine

HRID 2264176

反応式

HRID 2264176 の反応式
Cl[C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14](B(O)O)[CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[N+:9]([C:5]1[CH:4]=[CH:3][C:2]([C:14]2[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=2)=[N:7][C:6]=1[NH2:8])([O-:11])=[O:10]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 27343783-Pyridinylboronic acid

生成物 1

HCID 205503675-Nitro-2,3'-bipyridin-6-amine収率 77.1%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

An oven dried resealable Schlenk tube was charged with 6-chloro-3-nitropyridin-2-amine (5 g, 28.81 mmol), 3-pyridineboronic acid (5.31 g, 43.2 mmol), dioxane (250 mL) and a 2M aqueous solution of cesium carbonate (43 mL, 86.4 mmol). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (2.3 g, 2.81 mmol) was added. After three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in a 100° C. oil bath. After 3 h, the mixture was cooled, partitioned between water and ethyl acetate, the aqueous phase extracted twice with ethyl acetate, the organic layers washed with brine, dried (MgSO4) and evaporated. The residue was purified by silica gel flash chromatography (95:5 dichloromethane/methanol) to give the title compound (4.8 g, 77%) as a solid.

後処理

  1. customAn oven dried resealable Schlenk tube
  2. additionwas added
  3. customAfter three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped
  4. customplaced in a 100° C.
  5. temperaturethe mixture was cooled
  6. custompartitioned between water and ethyl acetate
  7. extractionthe aqueous phase extracted twice with ethyl acetate
  8. washthe organic layers washed with brine
  9. dry with materialdried (MgSO4)
  10. customevaporated
  11. customThe residue was purified by silica gel flash chromatography (95:5 dichloromethane/methanol)

出典と根拠

ORDレコード
ord-25d0255f5ad24c6ba3799fb65bb596f6
出典データセット
uspto-grants-2010_12
特許番号
US07855202B2

関連ノート

読み込み中…