反应详情

To a solution of 5-bromo-2-methyl-benzoic acid (1.35 g, 6.15 mmol) in THF (15 ml), CH2Cl2 (15 ml) and DMF (14.27 μl, 184.57 moles) is added dropwise oxalyl chloride (587.12 μl, 6.77 mmoles) at 0° C. and reaction mixture is slowly allowed to warm to ambient temperature. After 2 hours, the solvent is removed under reduced pressure. To the residue CH2Cl2 (30 ml) is added and reaction mixture is cooled to 0° C., then ethyl 4-amino-3,5-dimethyl-benzoate (1.19 g, 6.15 mmol) is added followed by 4-pyridinamine, N,N-dimethyl-(37.58 mg, 307.61 mmoles) and pyridine (1.49 ml, 18.46 mmoles). The cooling bath is removed and the clear solution is allowed to warm to ambient temperature. After 5 hours, the solvent is removed and the reaction mixture is diluted with ethyl acetate and washed with 1N HCl, saturated solution of sodium bicarbonate, and brine. The organic layers are combined and dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue is triturated with hexanes and the resulting solids were collected by filtration to give the title compound as a white solid (1.80 g; 75.2%). Mass spectrum (m/z): 390.2 (M+1).

1. customreaction mixture
2. customthe solvent is removed under reduced pressure
3. additionTo the residue CH2Cl2 (30 ml) is added
4. customreaction mixture
5. temperatureis cooled to 0° C.
6. customThe cooling bath is removed
7. temperatureto warm to ambient temperature
8. waitAfter 5 hours
9. customthe solvent is removed
10. additionthe reaction mixture is diluted with ethyl acetate
11. washwashed with 1N HCl, saturated solution of sodium bicarbonate, and brine
12. dry with materialdried over anhydrous Na2SO4
13. filtrationfiltered
14. concentrationconcentrated under reduced pressure
15. customThe resulting residue is triturated with hexanes
16. filtrationthe resulting solids were collected by filtration