Triphenylphosphine → 8-(1-Ethyl-propyl)-3-(3,5-dimethyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

HRID 226039

反応式

HRID 226039 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]=[C:25]([CH3:28])[CH:26]=[CH:27][C:22]=2[S:21][C:20]=1B(O)O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Ba+2].[OH-]>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].COCCOC.O>[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][C:25]([CH3:28])=[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 11776TriphenylphosphineHCID 6093286Barium hydroxideHCID 577526818-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazineHCID 68857091(3,5-Dimethylbenzo[b]thiophen-2-yl)boronic acid

生成物 1

HCID 577526068-(1-Ethyl-propyl)-3-(3,5-dimethyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazine収率 90%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 18180031Water 1,2-dimethoxyethane溶媒

反応条件

温度
90 °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), 3,5-dimethyl-benzothiophene-2-boronic acid (0.29 mmol), Pd2 dba3 (0.0072 mmol), triphenylphosphine (0.029 mmol), and barium hydroxide (0.435 mmol) in previously degassed mixture of DME/water [(2:1), 0.5 ml] is added to a pressure tube with a stirring bar. The mixture is degassed for 30 min. After heating for 16 h at 90° 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 tile compound (90%). 1H-NMR (CDCl3): 7.68 (m, 1H); 7.40 (m, 1H); 7.15 (m, 1H); 6.62 (s, 1H); 3.25 (m, 1H); 2.45 (s, 3H); 2.43 (s, 3H); 2.42 (s, 3H); 2.19 (s, 3H); 1.73 (m, 4H); 0.74 (t, 6H) ppm. MS/ES+=378 (M+1).

後処理

  1. additionis added to a pressure tube with a stirring bar
  2. customThe mixture 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-f2badbd18e8a44ca8639610f8ac8fe6e
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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