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

HRID 891862노트

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HRID 891862 반응식
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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

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온도
80 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-18e1a1e09ebd4c19be65d051caca8639
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07005431B2

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