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

HRID 347699

반응식

HRID 347699 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-adcf6c22613d4ec89aa12868dce46666
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176203B2

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