Triethylamine → 1-((2-methoxy-6-methylpyridin-3-yl)methyl)-4-nitro-3-vinyl-1H-indazole

HRID 79276노트

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HRID 79276 반응식
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:14][C:15]2[C:16]([O:22][CH3:23])=[N:17][C:18]([CH3:21])=[CH:19][CH:20]=2)[N:3]=1.[CH2:24](N(CC)CC)[CH3:25].[B-](F)(F)(F)C=C.[K+]>C(O)(C)C.O1CCCC1>[CH3:23][O:22][C:16]1[C:15]([CH2:14][N:4]2[C:5]3[C:10](=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][CH:6]=3)[C:2]([CH:24]=[CH2:25])=[N:3]2)=[CH:20][CH:19]=[C:18]([CH3:21])[N:17]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 672596093-iodo-1-((2-methoxy-6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazole

생성물 1

HCID 672606771-((2-methoxy-6-methylpyridin-3-yl)methyl)-4-nitro-3-vinyl-1H-indazole수율 52.7%

시약·촉매·용매 1

HCID 22597222Tetrahydrofuran 2-propanol용매

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온도
90 °C

실험 절차

A solution of 3-iodo-1-((2-methoxy-6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazole (982 mg, 2.31 mmol) in a 4:1 mixture of isopropyl alcohol/tetrahydrofuran (10 mL) was stirred under an argon atmosphere. Argon was bubbled through the solution for 20 minutes. Triethylamine (968 μL, 6.94 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (189 mg, 0.231 mmol) and potassium trifluoro(vinyl)borate (659 mg, 6.94 mmol) were added to the solution. The reaction mixture was heated at 90° C. for 24 hour. The mixture was allowed to cool and then filtered through Celite®, rinsing with ethyl acetate. The filtrate was concentrated under reduced pressure. The material was dissolved in ethyl acetate (50 mL), transferred to a reparatory funnel and washed with water and brine. The solution was dried over sodium sulfate, filtered and concentrated under reduced pressure. The material was purified using column chromatography on silica, eluting with 15-20% ethyl acetate in hexanes to give 1-((2-methoxy-6-methylpyridin-3-yl)methyl)-4-nitro-3-vinyl-1H-indazole (395 mg).

후처리

  1. customArgon was bubbled through the solution for 20 minutes
  2. temperatureto cool
  3. filtrationfiltered through Celite®
  4. washrinsing with ethyl acetate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. dissolutionThe material was dissolved in ethyl acetate (50 mL)
  7. customtransferred to a reparatory funnel
  8. washwashed with water and brine
  9. dry with materialThe solution was dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe material was purified
  13. washeluting with 15-20% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-deaded45f3d14db78b88fbeca26a0e4d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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