反应详情

To a solution of 4-iodo-3,5-dimethylisoxazole (for a preparation see intermediate 1, 142 g, 640 mmol, 1 eq.) and (3-aminophenyl)boronic acid (100 g, 640 mmol, 1 eq.) in DME (600 ml) were added tetrakis(triphenylphosphine) palladium(0) (18.5 g, 16 mol) and a solution of Na2CO3 (203.5 g, 192 mmol, 3 eq.) in water (750 ml). The mixture was heated under reflux for 24 h. To complete the reaction intermediate 1 (0.2 eq.) and tetrakis(triphenylphosphine) palladium(0) (5 g) were added and the mixture was refluxed overnight. The cooled mixture was poured into water and extracted with DCM. The organic phase was washed with water, dried over Na2SO4 and filtered. Evaporation of the solvent in vacuo gave a crude oil which was precipitated with iPr2O to afford the title compound as a beige solid (102 g, 85%). [ES-MS] m/z: 189 MH+, Rt 2.20 min.

1. temperatureThe mixture was heated
2. temperatureunder reflux for 24 h
3. additionwere added
4. temperaturethe mixture was refluxed overnight
5. extractionextracted with DCM
6. washThe organic phase was washed with water
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. customEvaporation of the solvent in vacuo
10. customgave a crude oil which
11. customwas precipitated with iPr2O