Реакция #1886977

Уравнение реакции

salicylaldoxime

3-chloro-1H-pyrazole

Cs2CO3

compound

5-Bromo-3-methylthiophene-2-carbaldehyde

→

title compound

Выход 38.0%

5-(3-chloro-1H-pyrazol-1-yl)-3-methylthiophene-2-carbaldehyde

Выход 38.0%

Растворители

MeCN

Условия реакции

Обработка

1. 1
   ДругоеThe tube was purged with N2
2. 2
   ТемператураAfter cooling to RT
3. 3
   workup.ADDITIONthe mixture was diluted with CH2Cl2 (10 mL)
4. 4
   Фильтрацияfiltered through a pad of CELITE®
5. 5
   КонцентрированиеThe filtrate was concentrated
6. 6
   Другоеpurified by flash chromatography (silica gel, hexanes:EtOAc, 100:0 to 50:50)

Методика

A sealed tube was charged with Copper(I) oxide (5.82 μL, 0.244 mmol), salicylaldoxime (134 mg, 0.975 mmol), 3-chloro-1H-pyrazole (500 mg, 4.88 mmol), Cs2CO3 (3178 mg, 9.75 mmol) and Part A compound of Example 1(150 mg, 7.32 mmol) and MeCN (4.877 mL). The tube was purged with N2 and the reaction stirred at 82° C. for 5 h. After cooling to RT, the mixture was diluted with CH2Cl2 (10 mL) and filtered through a pad of CELITE®. The filtrate was concentrated and purified by flash chromatography (silica gel, hexanes:EtOAc, 100:0 to 50:50) to afford 420 mg (38% yield) of the title compound as a brown solid: 1H NMR (500 MHz, CD3OD) δ 9.88 (1H, s), 8.34 (1H, s), 7.62 (1H, s), 7.07 (1H, s), 2.48 (3H, s). HPLC retention time 2.923 min., LCMS (ES): m/z 227 [M+H]+.

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