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

HRID 2264178

반응식

HRID 2264178 반응식
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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178479804HCID 178479804, 화합물촉매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-da3ea45afe0640649b9e02357679094a
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07855202B2

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