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Step 1: (6-Methyl-pyridin-3-yl)-methanol. To a stirred, cooled (0 C.) solution of 6-methyl nicotinic acid (5.0 mmol) in tetrahydrofuran (10 mL) was added lithium aluminum hydride (20 mmol; 20 mL of a 1solution in tetrahydrofuran.) dropwise. The reaction was stirred for 4 hours, treated sequentially with 1 mL of H2O, 1 mL of 15% aqueous sodium hydroxide, and 3 mL of H2O. The reaction was filtered and washed with tetrahydrofuran (3*50 mL). The filtrate was concentrated under reduced pressure to yield the alcohol as a clear viscous oil. Steps 2-3: Mitsunobu reaction and aniline deprotection according to the method of Compound 253.
N-(2,6-dimethoxyphenyl)-6-methylnicotinamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
68%
[0729j N-(2,6-dimethoxyphenyl)-6-methylnicotinamide, Example 370.1. To a stirred solution of 6-methylnicotinic acid (3.1 g, 22.8 mmol) and TEA (9.5 mL, 68.5 mmol) in DMF (76 mL) was added HATU (9.6 g, 25.1 mmol). After 3 mi 2,6- dimethoxyaniline (3.5 g, 22.9 mmol) was added. The resulting mixture was stirred at RT until LCMS analysis indicated that the reaction was complete. The reaction mixture was quenched using a mixture of saturated aqueous sodium bicarbonate and brine, then was extracted with EtOAc (4X). The combined organic layers were dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography (eluent: 25-100% EtOAc/hexanes) to provide 370.1 (4.2 g, 68% yield) as atan solid. LCMS-ESI (POS), mlz: 273.2 (M+H).
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