Cesium carbonate → 8-(1-Ethyl-propyl)-2,6-dimethyl-3-(3-methyl-benzo[b]thiophen-2-yl)-imidazo[1,2-b]pyridazine

HRID 226010

反応式

HRID 226010 の反応式
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13](I)=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].[CH3:18][C:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[S:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CN(C=O)C>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:20]3[S:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:19]=3[CH3:18])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 738173-Methylbenzo[b]thiopheneHCID 577526818-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine

生成物 1

HCID 577526258-(1-Ethyl-propyl)-2,6-dimethyl-3-(3-methyl-benzo[b]thiophen-2-yl)-imidazo[1,2-b]pyridazine収率 80%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

A mixture of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.145 mmol), 3-methyl-benzothiophene (7.25 mmol), Pd2 dba3 (0.0072 mmol), triphenylphosphine (0.029 mmol), and cesium carbonate (0.29 mmol) in previously degassed DMF (0.5 ml) is added to a pressure tube with a stirring bar. Mixture is degassed for 30 min. After heating for 16 h at 130° C., the reaction mixture is cooled, diluted with diethylether and washed with saturated aqueous ammonium chloride solution. The organic layer is dried over anhydrous magnesium sulfate, filtered, and the solvent is removed in vacuo. The residue is purified by silica gel column chromatography using mixtures of hexane-ethyl acetate as eluent to give the title compound (80%).

後処理

  1. additionis added to a pressure tube with a stirring bar
  2. customMixture is degassed for 30 min
  3. temperaturethe reaction mixture is cooled
  4. additiondiluted with diethylether
  5. washwashed with saturated aqueous ammonium chloride solution
  6. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent is removed in vacuo
  9. customThe residue is purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-43ac9d937e5c4f608cbb04b3b604d3a8
出典データセット
uspto-grants-2009_07
特許番号
US07557103B2

関連ノート

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