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

HRID 79363ノート

反応式

HRID 79363 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.[B-](F)(F)(F)[CH:25]=[CH2:26].[K+]>CC(O)C.C1COCC1>[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:25]=[CH2:26])=[N:3]2)=[CH:20][CH:19]=[C:18]([CH3:21])[N:17]=1

参加物

4

反応物 2

HCID 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 mixture of 3-iodo-1-((2-methoxy-6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazole (982 mg, 2.31 mmol) in 10 mL of 4:1 IPA/THF was degassed for 20 minutes with an argon balloon, to which TEA (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. The reaction mixture was heated at 90° C. for 3 hours. The mixture was filtered through Celite, and the filter pad was rinsed with ethyl acetate. The filtrate was washed with water and brine 3 times. The organic phase was concentrated to a residue under vacuum. The residue was purified by silica gel chromatography eluting with 15-20% EtOAc/hexanes to give the product (395 mg).

後処理

  1. additionwere added
  2. filtrationThe mixture was filtered through Celite
  3. washthe filter pad was rinsed with ethyl acetate
  4. washThe filtrate was washed with water and brine 3 times
  5. concentrationThe organic phase was concentrated to a residue under vacuum
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 15-20% EtOAc/hexanes

出典と根拠

ORDレコード
ord-a6890c3514524fd49755c6c5f74882e2
出典データセット
uspto-grants-2014_09
特許番号
US08841455B2

反応ノート

読み込み中…