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With sodium hydroxide; In ethanol; water; at 60.0℃; for 5.0h;
Methyl 7-bromo-1,5-naphthyridine-3-carboxylate (26 g, 98 mmol) was dissolved in ethanol (150 mL)Add 10% NaOH aqueous solution (260 mL), add the reaction solution to 60 C for 5 h, and evaporate to remove ethanol.Adjust the pH to 4-6 with 2M hydrochloric acid, precipitate a solid, and filter with suction.Drying gave the desired product 7-bromo-1,5-naphthyridin-3-carboxylic acid (25 g, white solid, yield 99%).
Example 667-BROMO-[1,5]NAPHTHYRIDINE-3-CARBOXYLIC ACID [(R)-1-(2-FLUORO-4-METHANE-SULFONYLAMINO-5-METHYL-PHENYL)-ETHYL]-AMIDE 66A) To a solution of <strong>[958334-24-2]methyl 7-bromo-1,5-naphthyridine-3-carboxylate</strong> (200 mg; 0.70 mmol) in Methanol (3 mL, 70 mmol), 1N Sodium hydroxide in water (3 mL, 3 mmol) was added and the reaction was stirred at room temperature 2 h. The reaction mixture was neutralized with 1N HCl, dried (MgSO4), filtered and evaporated. The crude residue was used in the next step without further purification. m/z=255.11 (M+1), r.t. 2.56 min.
With N-Bromosuccinimide; acetic acid; at 100.0℃; for 6.0h;
Methyl 1,5-naphthyridin-3carboxylate (17.5 g, 93.0 mmol), acetic acid (150 mL) was mixed and heated to 100 C,N-bromosuccinimide (17.4 g, 97.7 mmol) was added portionwise, and the reaction was carried out at 100 C for 6 h.The reaction was monitored by TLC.Spin dry, add 1 water (100 mL), stir, filter, filter cake wash, EA wash,Drying gave 7-bromo-1,5-naphthyridin-3-carboxylic acid methyl ester (22.5 g, white solid, yield 92%).
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