Реакция #44183

Уравнение реакции

4-Bromo-2-fluorophenylamine

4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid

i-Pr2NH

n-BuLi

→

desired product

Выход 77.0%

4-(4-bromo-2-fluorophenylamino)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid

Выход 77.0%

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   workup.STIRRINGAfter vigorous stirring for 10 minutes
2. 2
   workup.ADDITIONwas added
3. 3
   ДругоеThe dry-ice bath was removed after 30 minutes
4. 4
   workup.STIRRINGthe reaction mixture was stirred for 17 hours at room temperature
5. 5
   workup.ADDITIONThe reaction mixture was treated with a 10% aqueous HCl solution (15 mL)
6. 6
   Экстракцияextracted with EtOAc
7. 7
   Сушкаdried (MgSO4)
8. 8
   Концентрированиеconcentrated

Методика

To a solution of i-Pr2NH (0.39 mL, 2.80 mmol) in THF (4 mL) at 0° C. was added n-BuLi (1.1 mL, 2.80 mmol, 2.5 M solution in hexanes). After stirring 15 minutes, the mixture was cooled to −78° C. 4-Bromo-2-fluorophenylamine (0.38 g, 2.0 mmol) was added. After vigorous stirring for 10 minutes, a mixture of the 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid (0.15 g, 0.80 mmol) in THF (5 mL) was added. The dry-ice bath was removed after 30 minutes, and the reaction mixture was stirred for 17 hours at room temperature. The reaction mixture was treated with a 10% aqueous HCl solution (15 mL), extracted with EtOAc, dried (MgSO4), and concentrated. Trituration with methylene chloride gave 0.21 g (77%) desired product. MS APCI (−) m/z 339, 341 (M−, Br pattern) detected; 1H NMR (400 MHz, DMSO-d6) δ 9.61 (s, 1H), 8.53 (s, 1H), 7.69 (dd, 1H), 7.46 (m, 2H), 3.41 (s, 3H).

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