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

HRID 79363노트

반응식

HRID 79363 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.[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

참가 물질

4

반응물 2

HCID 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

반응 조건

온도
90 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a6890c3514524fd49755c6c5f74882e2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

반응 노트

불러오는 중…