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With diphenyl phosphoryl azide; triethylamine; at 20℃; for 4.08333h;Heating / reflux;
methyl 3- [(fe^-butoxycarbonyl)aminolpyridine-2-carboxylate; To a mixture of 2- (methoxycarbonyi)nicotinic acid and 3-(methoxycarbonyl)pyridine-2-carboxylic acid (10.46 g, 57.7 mmol) is added tert-butanol (100 mL) and TEA (8.85 mL, 63.5 mmol). The reaction is stirred for five minutes at rt and then diphenyl phosphoryl azide (13.1 mL, 60.6 mmol) is added. The reaction is heated to reflux and stirred for approximately four hours. The reaction mixture is cooled to rt, concentrated to dryness, re-dissolved in EtOAc, and washed with water and saturated sodium bicarbonate (2 x 20 mL each). The organic layers are combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The mixture is purified by column chromatography (100% hexanes to 100% EtOAc) to yield the title compound and methyl 2-[(f°rt-butoxycarbonyl)amino]nicotinate (9.24 g, 64% yield). LCMS (ES, M+Na=275).
2-(Methoxycarbonyl)pyridine-3-carboxylic acid (3 g, 16.57 mmol) was dissolved in 50 mL of t-ButOH and 4 mL of TEA were added. The solution was stirred for 5 min at room temperature, then diphenylphosphorylazide (3.6 mL, 16.57 mmol) was added and the reaction was refluxed for 3 hours. The mixture was concentrated and the residue purified flash chromatography (silica) eluting with ethyl acetate in cyclohexane from 20 to 50%. The fractions containing the product were collected and concentrated in vacuo to give methyl 3-[(tert- butoxy)carbonyl]amino}pyridine-2-carboxylate (1.6 g, 38.5% yield).
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