반응 #1798969
ord-3a5fe81c8d12404ca796bc8ef8502798
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시약
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후처리
- 1기타prepared
- 2온도the mixture was warmed to ambient temperature
- 3workup.STIRRINGthe mixture was stirred overnight
- 4기타the layers were separated
- 5건조The organic solution was dried over MgSO4
- 6여과filtered
- 7기타The filtrate was evaporated
- 8기타then purified by flash chromatography on 10 g silica gel with 95:5 DCM/MeOH as an eluent
- 9기타to give a residue that
- 10기타was triturated with Et2O/heptane
실험 절차
The ethyl 6-(6-(4-fluorophenyl)imidazo[2,1-b]oxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridine-3-carboxylate (0.250 g, 0.639 mmol; prepared using A from 6-(4-fluorophenyl)-imidazo[2,1-b]oxazole [prepared according to WO2004110990A2, Example 1, Steps 1-3] with NIS, C with 2-fluoropyridine-5-boronic acid [Asymchem], D with hydrazine, K.1 with ethyl 2-oxoacetate) was suspended in THF (2.5 mL) then cooled to about −78° C. Methylmagnesium bromide (1.4 M in THF, 1.0 mL, 1.40 mmol) was added and then the mixture was warmed to ambient temperature. Additional methylmagnesium bromide (0.20 mL; 0.28 mmol) was added and then the mixture was stirred for about 15 min. Saturated aqueous ammonium chloride solution (1-2 mL) was added and then the mixture was stirred overnight. The reaction was diluted with DCM and then the layers were separated. The organic solution was dried over MgSO4 and then filtered. The filtrate was evaporated then purified by flash chromatography on 10 g silica gel with 95:5 DCM/MeOH as an eluent to give a residue that was triturated with Et2O/heptane to give the title compound (0.010 g, 4.1% yield): LC/MS (Table 1, Method a) Rt=1.89 min; MS m/z: 378.1 (M+H)+.