Cesium carbonate → 7-(Furan-3-yl)-3-[3-(pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridine

HRID 985525ノート

反応式

HRID 985525 の反応式
Cl[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:12]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1.[O:23]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.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].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[NH3:5].[O:23]1[CH:27]=[CH:26][C:25]([C:2]2[CH:7]=[CH:6][N:5]3[C:8]([C:11]4[CH:16]=[CH:15][CH:14]=[C:13]([C:17]5[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=5)[CH:12]=4)=[CH:9][N:10]=[C:4]3[CH:3]=2)=[CH:24]1

参加物

8

反応物 3

HCID 10796Cesium carbonateHCID 2734358Furan-3-boronic acidHCID 99011257-Chloro-3-[3-(pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridine

生成物 2

HCID 222AmmoniaHCID 99457517-(Furan-3-yl)-3-[3-(pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridine収率 37%

試薬・触媒・溶媒 3

HCID 83681Tris(1,1-dimethylethyl)phosphine触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

7-Chloro-3-[3-(pyridin-3-yl)phenyl]imidazo[1,2-α]pyridine (0.27 g, 0.88 mmol), 3-furanboronic acid (0.15 g, 1.33 mmol and caesium carbonate (0.58 g, 1.77 mmol) were suspended in 1,4-dioxane (5 ml) under an atmosphere of nitrogen. Tris(dibenzylideneacetone)dipalladium(0) (12 mg, 0.015 mmol) and tri-tert-butylphosphine (6.5 mg, 0.032 mmol) were then added and the mixture heated at 90° C. for 24 h. The mixture was cooled and partitioned between dichloromethane and water. The organic layer was washed with brine, dried over sodium sulphate and concentrated in vacuo to give a brown oil. Purification by flash column chromatography eluting with dichloromethane/methanol/conc. ammonia (98:2:0.2) gave the title compound (110 mg, 37%) as a pale yellow crystalline solid, m.p. 158-160° C. 1H NMR (360 MHz, CDCl3) δH 6.79 (1H, s), 6.96-7.02 (1H, m), 7.39-7.43 (1H, m), 7.52-7.56 (1H, m), 7.59-7.69 (2H, m), 7.75-7.91 (8H, m), 8.32-8.37 (1H, m), 8.63-8.68 (1H, m), 8.92 (1H, s); m/z (ES+) 338 (M++H).

後処理

  1. temperatureThe mixture was cooled
  2. custompartitioned between dichloromethane and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customto give a brown oil
  7. customPurification by flash column chromatography
  8. washeluting with dichloromethane/methanol/conc

出典と根拠

ORDレコード
ord-82960f99ce404a778c936a6091bfffc9
出典データセット
uspto-grants-2005_03
特許番号
US06872731B2

反応ノート

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