反应详情

To a solution of 6-chloro-3-methyl-pyridine-2-carboxylic acid (465 mg, 2.71 mmol) in THF (5 ml), CH2Cl2 (5 ml) and DMF (0.01 ml, 129.33 μmoles) is added dropwise oxalyl chloride (0.3 ml, 3.46 mmoles) at 0° C. and the reaction mixture is slowly allowed to warm to ambient temperature. After 2 hours, the solvent is removed under reduced pressure. To the residue CH2Cl2 (20 ml) is added and reaction mixture is cooled to 0° C., then methyl 3-amino-3,5-dimethylbenzoate (490 mg, 2.73 mmol) is added followed by N,N-dimethylpyridin-4-amine (15 mg, 122.78 μmoles) and pyridine (0.66 ml, 8.16 mmoles). The cooling bath is removed and the clear solution is allowed to warm to ambient temperature. After 1.5 hours, the solvent is removed and the reaction mixture is diluted with ethyl acetate and washed with 0.5N HCl, saturated solution of sodium bicarbonate, and brine. The organic layers are combined and dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give the title compound as a light yellow solid (664 mg, 73%). Mass spectrum (m/z): 333.2 (M+1).

1. customthe solvent is removed under reduced pressure
2. additionTo the residue CH2Cl2 (20 ml) is added
3. customreaction mixture
4. temperatureis cooled to 0° C.
5. customThe cooling bath is removed
6. temperatureto warm to ambient temperature
7. waitAfter 1.5 hours
8. customthe solvent is removed
9. additionthe reaction mixture is diluted with ethyl acetate
10. washwashed with 0.5N HCl, saturated solution of sodium bicarbonate, and brine
11. dry with materialdried over anhydrous Na2SO4
12. filtrationfiltered
13. concentrationconcentrated under reduced pressure