Sodium Carbonate → 4-(3-Trifluoromethylimidazo[1,2-b][1,2,4]triazin-7-yl)-[2,4']bipyridinyl

HRID 347699

反応式

HRID 347699 の反応式
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[N:7][N:6]2[C:9]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([C:18]4[CH:25]=[CH:24]C=C[C:19]=4[C:20]#[N:21])[CH:13]=3)=[CH:10][N:11]=[C:5]2[N:4]=1.N1C=CC(B(O)O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]([F:26])([F:27])[C:3]1[CH:8]=[N:7][N:6]2[C:9]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([C:18]4[CH:25]=[CH:24][N:21]=[CH:20][CH:19]=4)[CH:13]=3)=[CH:10][N:11]=[C:5]2[N:4]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 99071722-[4-(3-Trifluoromethylimidazo[1,2-b][1,2,4]triazin-7-yl)pyridin-2-yl]-benzonitrile

生成物 1

HCID 100429834-(3-Trifluoromethylimidazo[1,2-b][1,2,4]triazin-7-yl)-[2,4']bipyridinyl収率 24.8%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

A mixture of 7-(2-chloropyridin-4-yl)-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (0.10 g, 0.33 mmol) (prepared as described in Example 1), pyridine-4-boronic acid (50 mg, 0.40 mmol) and sodium carbonate (600 μl of a 2 M solution) in 1,4-dioxane (3 ml) was degassed by bubbling nitrogen through for 20 min. Tetrakis(triphenylphosphine)palladium(0) (50 mg, 0.04 mmol) was added and the mixture heated at 90° C. for 4 h. Solvent was removed in vacuo from the mixture and the residue partitioned between dichloromethane (50 ml) and water (30 ml). The organic layer was washed with saturated brine then dried (MgSO4), filtered and evaporated in vacuo. Purification by chromatography (silica gel, 5% MeOH/CH2Cl2) gave 28 mg of the title compound as a yellow solid: 1H NMR (400 MHz, CDCl3) δ 7.98–7.99 (2H, m), 8.06 (1H, dd, J 1.6, 5.1), 8.59 (1H, s), 8.79–8.84 (3H, m), 8.94 (1H, dd, J 0.8, 4.3), 8.95 (1H, s); MS (ES+) m/z 343 [M+H]+.

後処理

  1. customwas degassed
  2. customby bubbling nitrogen through for 20 min
  3. customSolvent was removed in vacuo from the mixture
  4. customthe residue partitioned between dichloromethane (50 ml) and water (30 ml)
  5. washThe organic layer was washed with saturated brine
  6. dry with materialthen dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customPurification by chromatography (silica gel, 5% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-adcf6c22613d4ec89aa12868dce46666
出典データセット
uspto-grants-2007_02
特許番号
US07176203B2

関連ノート

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