반응 #626986

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3-bromo-N-[2-[3-(2,2-dimethylpropanoylamino)-4-methyl-phenyl]imidazo[2,1-f]pyridazin-6-yl]benzamide

Ethyl acrylate

tri(o-tolyl)phosphine

DIPEA

→

title compound

수율 30.4%

ethyl-3-[3-[[2-[3-(2,2-dimethylpropanoylamino)-4-methyl-phenyl]imidazo[2,1-f]pyridazin-6-yl]carbamoyl]phenyl]prop-2-enoate

수율 30.4%

용매

DMF

반응 조건

후처리

1. 1
   기타The mixture is degassed with N2
2. 2
   기타then sealed
3. 3
   온도The reaction mixture is cooled
4. 4
   workup.ADDITIONsaturated aqueous NaHCO3 (50 mL) added
5. 5
   추출extracted with EtOAc (×3)
6. 6
   세척washed with water, NaHCO3, brine
7. 7
   기타dried
8. 8
   농축concentrated
9. 9
   기타purified by silica gel chromatography (0-100% EtOAc in Hexanes)

실험 절차

To a mixture of 3-bromo-N-[2-[3-(2,2-dimethylpropanoylamino)-4-methyl-phenyl]imidazo[2,1-f]pyridazin-6-yl]benzamide (0.126 g, 0.25 mmol), Ethyl acrylate (0.272 mL, 2.5 mmol), palladium(II) acetate (2.8 mg, 0.01 mmol), tri(o-tolyl)phosphine (0.0152 g, 0.05 mmol) in DMF (1.45 mL) is added DIPEA (0.174 mL, 1 mmol). The mixture is degassed with N2 then sealed and heated at 110° C. for 18 hours. The reaction mixture is cooled, saturated aqueous NaHCO3 (50 mL) added and extracted with EtOAc (×3). Organic layers are combined and washed with water, NaHCO3, brine, then dried, concentrated and purified by silica gel chromatography (0-100% EtOAc in Hexanes) to give the title compound (0.040 g). LCMS (m/z)=526.6 [M+H]+, tR=2.92 min.

출처