تفاعل #602395

معادلة التفاعل

5-bromo-1-(cyclopropylmethyl)-3-methyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

cesium carbonate

dioxane

→

2-[1-(cyclopropylmethyl)-3-methyl-2,2-dioxido-1,3-dihydro-2,1,3-benzothiadiazol-5-yl]benzonitrile

المذيبات

methanol

water

ظروف التفاعل

المعالجة

1. 1
   أخرىThe crude reaction mixture
2. 2
   درجة الحرارةto cool to room temperature
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated
5. 5
   أخرىPurification of crude
6. 6
   أخرىreaction mixture by reverse phase chromatography (Waters Sunfire MSC18, 10% acetonitrile/0.1% trifluoroacetic acid/water→100% acetonitrile/0.1% trifluoroacetic acid/water)

الإجراء التجريبي

To a microwave vial was added 5-bromo-1-(cyclopropylmethyl)-3-methyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (1-4) (0.074 g, 0.23 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (0.070 g, 0.30 mmol), cesium carbonate (0.15 g, 0.47 mmol), palladium bis(tri-tert-butylphosphine) (0.024 g, 0.047 mmol), dioxane (1 mL), and water (0.2 mL). The reaction mixture was then heated under microwave irradiation at 100° C. for 10 minutes. The crude reaction mixture was then allowed to cool to room temperature, diluted with methanol, then filtered and concentrated. Purification of crude reaction mixture by reverse phase chromatography (Waters Sunfire MSC18, 10% acetonitrile/0.1% trifluoroacetic acid/water→100% acetonitrile/0.1% trifluoroacetic acid/water) to give 2-[1-(cyclopropylmethyl)-3-methyl-2,2-dioxido-1,3-dihydro-2,1,3-benzothiadiazol-5-yl]benzonitrile (1-5). 1H NMR (400 MHz, CD3 OD): δ 7.82 (d, J=7.8 Hz, 1 H); 7.72 (t, J=7.7 Hz, 1 H); 7.61 (d, J=7.9 Hz, 1 H); 7.51 (t, J=7.7 Hz, 1 H); 7.22 (d, J=8.2 Hz, 1 H); 7.15-7.07 (m, 2H); 3.70 (d, J=6.8 Hz, 2 H); 3.31 (s, 3 H); 1.39-1.30 (m, 1 H); 0.66 (d, J=7.7 Hz, 2 H); 0.49 (d, J=5.1 Hz, 2 H). HRMS (M+H)+: observed=340.1114, calculated=340.1114.

المصدر