Sodium Carbonate → 7-[2,4-Difluoro-3-(pyridin-3-yl)phenyl]-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine

HRID 891862ノート

反応式

HRID 891862 の反応式
Br[C:2]1[N:6]2[N:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[N:10][C:5]2=[N:4][CH:3]=1.[F:15][C:16]1[C:21]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[C:20]([F:28])[CH:19]=[CH:18][C:17]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[F:28][C:20]1[C:21]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[C:16]([F:15])[CH:17]=[CH:18][C:19]=1[C:2]1[N:6]2[N:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[N:10][C:5]2=[N:4][CH:3]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 116014167-Bromo-3-trifluoromethyl-imidazo[1,2-B][1,2,4]triazineHCID 222400962,4-Difluoro-3-(pyridin-3-yl)benzeneboronic acid

生成物 1

HCID 99996397-[2,4-Difluoro-3-(pyridin-3-yl)phenyl]-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine収率 55.9%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

A mixture of 7-bromo-3-trifluoromethylimidazo[1,2-b][1,2,4]triazine (0.1 g, 0.37 mmol), 2,4-difluoro-3-(pyridin-3-yl)benzeneboronic acid (132 mg, 0.56 mmol) and 2 M Na2CO3 (0.56 ml) in 1,2-dimethoxyethane (2 ml) was degassed for 10 min with a stream of nitrogen. Tetrakis(triphenylphosphine)palladium(0) (0.022 g) was added and the mixture was stirred under nitrogen at 80° C. for 12 h. After allowing to cool to ambient temperature, the mixture was diluted with ethyl acetate then partitioned between water (100 ml) and ethyl acetate (100 ml). The organic extracts were dried (MgSO4), filtered and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 2.5% MeOH/CH2Cl2), to give 78 mg (55%) of the title compound: 1H NMR (400 MHz, CDCl3) δ 7.17–7.22 (1H, m), 7.37–7.41 (1H, m), 7.80 (1H, d, J 8.4), 8.10–8.16 (1H, m), 8.56 (1H, d, J 2.6), 8.62 (1H, dd, J 4.6, 1.5), 8.72 (1H, 8.74 (1H, s); MS (ES+) m/z 378 [M+H]+.

後処理

  1. customwas degassed for 10 min with a stream of nitrogen
  2. additionTetrakis(triphenylphosphine)palladium(0) (0.022 g) was added
  3. temperatureto cool to ambient temperature
  4. additionthe mixture was diluted with ethyl acetate
  5. customthen partitioned between water (100 ml) and ethyl acetate (100 ml)
  6. dry with materialThe organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was purified by flash chromatography (silica gel, 2.5% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-18e1a1e09ebd4c19be65d051caca8639
出典データセット
uspto-grants-2006_02
特許番号
US07005431B2

反応ノート

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