Methanol → Methyl 3-({4-[(dimethylamino)carbonyl]phenyl}amino)-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate

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Reaction Steps

3-({4-[(dimethylamino)carbonyl]phenyl} amino)-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylic acid (79 mg, 0.201 mmol) was dissolved in a 9:1 acetonitrile:methanol solution (5 mL) and trimethylsilyldiazomethane (0.3 mL, 0.603 mmol) was added and the reaction was stirred at ambient temperature until complete by TLC (10% methanol/dichloromethane). The mixture was concentrated under reduced pressure, aqueous sodium bicarbonate was added, and the aqueous layer was extracted with chloroform. The combined organics were washed with brine and dried over sodium sulfate to yield methyl 3-({4-[(dimethylamino)carbonyl]phenyl}amino)-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate (40.5 mg, 49% yield). 1H NMR (CDCl3) δ 9.49 (s, 1 H), 8.00 (s, 1 H), 7.34-7.36 (m, 3 H), 7.12-7.05 (m, 4 H), 6.97-6.94 (m, 2 H), 3.97 (s, 3 H), 3.87 (s, 2 H), 3.07 (br s, 3 H), 3.02 (br s, 3 H); MS m/z 408 (M+1).

Provenance & Evidence