Methacrylamide → (E)-3-(3-(5-amino-3-(2-fluorophenyl)-1H-pyrazol-1-yl)phenyl)-2-methylacrylamide

HRID 1696591노트

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HRID 1696591 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:12]=[C:11]([NH2:13])[N:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16](I)[CH:15]=2)[N:9]=1.[C:21]([NH2:26])(=[O:25])[C:22]([CH3:24])=[CH2:23].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(CC)CC>CN(C=O)C.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[NH2:13][C:11]1[N:10]([C:14]2[CH:15]=[C:16](/[CH:23]=[C:22](\[CH3:24])/[C:21]([NH2:26])=[O:25])[CH:17]=[CH:18][CH:19]=2)[N:9]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[CH:12]=1

참가 물질

8

반응물 4

HCID 6595MethacrylamideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 672720773-(2-Fluorophenyl)-1-(3-iodophenyl)-1H-pyrazol-5-amine

생성물 1

HCID 67270652(E)-3-(3-(5-amino-3-(2-fluorophenyl)-1H-pyrazol-1-yl)phenyl)-2-methylacrylamide수율 95%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

3-(2-Fluorophenyl)-1-(3-iodophenyl)-1H-pyrazol-5-amine (0.500 g, 1.32 mmol, 1.00 eq), methacrylamide (0.281 g, 3.30 mmol, 2.50 eq), Pd(OAc)2 (0.0118 g, 0.0527 mmol, 0.04 eq), Ph3P (0.0346 g, 0.132 mmol, 0.10 eq) and Et3N (0.919 ml, 6.59 (mmol, 5.00 eq) were combined in DMF (3 ml) and heated at 80° C. overnight. The reaction was cooled to RT, diluted with H2O and extracted with EtOAc (2×). The combined organics were washed with 5% citric acid (2×), brine (1×) and dried (MgSO4). Filtration and evaporation gave crude product which was purified by flash chromatography to afford 0.4192 g (95%) of pure (E)-3-(3-(5-amino-3-(2-fluorophenyl)-1H-pyrazol-1-yl)phenyl)-2-methylacrylamide. MS (ESI) m/z: 337.2 (M+H+).

후처리

  1. temperatureThe reaction was cooled to RT
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organics were washed with 5% citric acid (2×), brine (1×)
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and evaporation
  6. customgave crude product which
  7. customwas purified by flash chromatography

출처 및 근거

ORD 기록
ord-30c7ffdd97714068b5823360bdcc3e36
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163756B2

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