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

HRID 79276ノート

反応式

HRID 79276 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 22597222Tetrahydrofuran 2-propanol溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-deaded45f3d14db78b88fbeca26a0e4d
出典データセット
uspto-grants-2014_09
特許番号
US08841455B2

反応ノート

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