Sodium Carbonate → 3-(3-Chloro-phenyl)-imidazo[1,2-a]pyridine-7-carboxylic acid sodium salt

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Reaction Steps

A mixture of 3-iodo-imidazo[1,2-a]pyridine-7-carboxylic acid methyl ester (230 mg, 0.76 mmol), Pd(PPh3)4 (44 mg, 0.038 mmol), Na2CO3 (161 mg, 1.52 mmol) and 3-chlorophenylboronic acid (131 mg, 0.84 mmol) was heated at reflux for 1 hour. The mixture was then allowed to cool and concentrated in vacuo. The residue was dissolved in MeOH (25 mL) and water (25 mL) and 50% NaOH (5 mL) was added. The mixture was allowed to stir at room temperature for 15 hours then concentrated in vacuo. The mixture was triturated with ethyl acetate (20 mL) and the resulting solid was filtered to afford 3-(3-chloro-phenyl)-imidazo[1,2-a]pyridine-7-carboxylic acid sodium salt (100 mg, 58%) The mixture was dissolved in DMF (2 mL) and EDC (100 mg, 0.52 mmol) and HOBt (70 mg, 0.52 mmol) were added. The mixture was allowed to stir for 10 minutes and 4-aminomethyltetrahydropyran (0.075 mL, 0.52 mmol) was added. The mixture was stirred for 2 hours then poured into water (15 mL) and the product extracted with ethyl acetate (2×50 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3-(3-chlorophenyl)-imidazo[1,2-a]pyridine-7-carboxylic acid (tetrahydro-pyran-4-ylmethyl)-amide. 1H NMR (DMSO-d6) δ 8.75 (1H), 8.65 (1H), 8.25 (1H), 8.00 (1H), 7.80 (1H), 7.70 (1H), 7.60 (1H), 7.52 (1H), 7.41 (1H), 3.85 (2H), 3.32 (2H), 3.20 (2H), 1.83 (1H), 1.60 (2H), 1.22 (2H); m/z (M+H)=370.05.

Provenance & Evidence