Реакция #67737

Уравнение реакции

6-chloro-5-methylpyridin-2-amine

triethylamine

1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride

→

N-(6-chloro-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   ДругоеThe resulting reaction mixture
2. 2
   ПромывкаThe reaction mixture was then washed with 1N aqueous NaOH (2×200 mL), 1N aqueous HCl (1×200 mL) and saturated aqueous NaHCO3 (1×200 mL)
3. 3
   СушкаThe organics were dried over sodium sulfate
4. 4
   Другоеevaporated
5. 5
   Другоеto yield the product (26.9 g, 73.3 mmol, 94% 2-step)

Методика

To a solution of 6-chloro-5-methylpyridin-2-amine (11.1 g, 78 mmol) and triethylamine (22.0 mL, 156 mmol) in dichloromethane (100 mL) was added a solution of 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride (20.3 g, 78 mmol) in dichloromethane (50 mL). The resulting reaction mixture was allowed to stir at room temperature for eighteen hours. The reaction mixture was then washed with 1N aqueous NaOH (2×200 mL), 1N aqueous HCl (1×200 mL) and saturated aqueous NaHCO3 (1×200 mL). The organics were dried over sodium sulfate and evaporated to yield the product (26.9 g, 73.3 mmol, 94% 2-step). ESI-MS m/z calc. 366.06. found 367.3 (M+1)+. Retention time 2.19 minutes. 1H NMR (400 MHz, DMSO-d6) δ 9.30 (s, 1H), 7.89-7.87 (m, 1H), 7.78-7.76 (m, 1H), 7.54-7.53 (m, 1H), 7.41-7.39 (m, 1H), 7.33-7.30 (m, 1H), 2.26 (s, 3H), 1.52-1.49 (m, 2H), 1.19-1.16 (m, 2H).

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