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

HRID 1696591ノート

反応式

HRID 1696591 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-30c7ffdd97714068b5823360bdcc3e36
出典データセット
uspto-grants-2012_04
特許番号
US08163756B2

反応ノート

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