3-Fluoro-4-(tributylstannyl)pyridine → 3''-Fluoro-5'-nitro-3,2':3',4''-terpyridin-6'-amine

HRID 2264178

反応式

HRID 2264178 の反応式
Br[C:2]1[C:3]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[N:4][C:5]([NH2:11])=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[F:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:24]=1[Sn](CCCC)(CCCC)CCCC>C1(P([Pd-](Cl)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I.CN(C)C=O>[F:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:24]=1[C:2]1[C:3]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[N:4][C:5]([NH2:11])=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

参加物

6

反応物 2

HCID 222736013-Fluoro-4-(tributylstannyl)pyridineHCID 595960023-Bromo-5-nitro-2,3'-bipyridin-6-amine

生成物 1

HCID 595960063''-Fluoro-5'-nitro-3,2':3',4''-terpyridin-6'-amine収率 51%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178479804HCID 178479804、化合物触媒HCID 6228Dimethylformamide溶媒

実験手順

An oven dried resealable Schlenk tube was charged with 3-bromo-5-nitro-2,3′-bipyridin-6-amine (4.51 g, 15.3 mmol), 3-fluoro-4-(tributylstannyl)pyridine (11.8 g, 30.6 mmol) and dimethylformamide (150 mL). The Schienk tube was subjected to three cycles of evacuation-backfilling with argon, and bis(triphenylphosphino)-palladium (II) chloride (1.1 g, 1.53 mmol) and copper (I) iodide (291 mg, 1.53 mmol) were added. After three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in a 160° C. oil bath. After 3 h, the solvent was evaporated and the crude residue was treated with 2N hydrogen chloride (130 mL) aqueous solution for 45 minutes. The aqueous solution was washed with ethyl acetate and then neutralised with 6N sodium hydroxide aqueous solution. The solution was extracted with ethyl acetate, dried (MgSO4) and evaporated. The residue was purified by silica gel flash chromatography (95:5 dichloromethane/methanol) to give the title compound (2.39 g, 51%) as a solid.

後処理

  1. customAn oven dried resealable Schlenk tube
  2. additionwere added
  3. customAfter three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped
  4. customplaced in a 160° C.
  5. customthe solvent was evaporated
  6. additionthe crude residue was treated with 2N hydrogen chloride (130 mL) aqueous solution for 45 minutes
  7. washThe aqueous solution was washed with ethyl acetate
  8. extractionThe solution was extracted with ethyl acetate
  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-da3ea45afe0640649b9e02357679094a
出典データセット
uspto-grants-2010_12
特許番号
US07855202B2

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