反应 #554655

反应方程式

2-iodo-5-methylbenzoic acid

1,2,3-triazole

trans-N,N′-dimethylcyclohexane-1,2-diamine

→

2-(2H-1,2,3-Triazol-2-yl)-5-methylbenzoic acid

溶剂

water

DMF

反应条件

后处理

1. 1
   温度The reaction was cooled to room temperature
2. 2
   洗涤washed with EtOAc
3. 3
   萃取extracted with EtOAc
4. 4
   干燥The organic layer was dried over Na2SO4
5. 5
   过滤filtered
6. 6
   浓缩concentrated
7. 7
   其他The residue was purified by gradient elution on SiO2 (0 to 10% MeOH in water with 0.1% AcOH)
8. 8
   其他to give the
9. 9
   洗涤faster eluting 2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid 1-5

实验过程

A solution of 2-iodo-5-methylbenzoic acid (4.0 g, 15.3 mmol) in DMF (10 mL) was treated with 1,2,3-triazole (2.1 g, 30.5 mmol), CsCO3 (9.95 g, 30.5 mmol), CuI (0.145 g, 0.76 mmol) and trans-N,N′-dimethylcyclohexane-1,2-diamine (0.43 g, 3.05 mmol). The mixture was heated at 120° C. for 10 min in a microwave reactor. The reaction was cooled to room temperature, diluted with water, and washed with EtOAc. The aqueous phase was acidified with 1N HCl and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by gradient elution on SiO2 (0 to 10% MeOH in water with 0.1% AcOH) to give the faster eluting 2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid 1-5, followed by the undesired regioisomer isomer, 1-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid. Data for 1-7: 1HNMR (500 MHz, DMSO-d6)d 12.98 (br s, 1H), 8.04 (s, 2H), 7.72-7.45 (m, 3H), 2.41 (s, 3H) ppm.

来源