Реакция #531825

Уравнение реакции

potassium carbonate

2,3-dichloropyridine

3-bromopyrazole

product

3-bromopyrazole

→

pink solid

2-(3-bromo-1H-pyrazol-1-yl)-3-chloropyridine

Растворители

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   ТемператураThe reaction mixture was cooled to room temperature
2. 2
   ДругоеA precipitate formed
3. 3
   Фильтрацияfiltered
4. 4
   Промывкаwashed with water (2×100 mL)
5. 5
   ФильтрацияThe solid filter cake
6. 6
   Промывкаwashed sequentially with water, 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution, and brine
7. 7
   СушкаThe organic extracts were then dried over magnesium sulfate
8. 8
   Концентрированиеconcentrated

Методика

To a mixture of 2,3-dichloropyridine (27.4 g, 185 mmol) and 3-bromopyrazole (i.e. the product of Step B) (25.4 g, 176 mmol) in dry N,N-dimethylformamide (88 mL) was added potassium carbonate (48.6 g, 352 mmol), and the reaction mixture was heated to 125° C. for 18 hours. The reaction mixture was cooled to room temperature and poured into ice water (800 mL). A precipitate formed. The precipitated solids were stirred for 1.5 h, filtered and washed with water (2×100 mL). The solid filter cake was taken up in methylene chloride and washed sequentially with water, 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution, and brine. The organic extracts were then dried over magnesium sulfate and concentrated to afford 39.9 g of a pink solid. The crude solid was suspended in hexane and stirred vigorously for 1 hr. The solids were filtered, washed with hexane and dried to afford the title product as an off-white powder (30.4 g) determined to be >94% pure by NMR. This material was used without further purification in Step D.

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