تفاعل #67107

معادلة التفاعل

HCl

HCl

DCM

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

2,4-difluorobenzenesulfonyl chloride

→

title compound

المردود 84.1%

2,4-Difluoro-N-[2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]benzenesulfonamide

المردود 84.1%

المذيبات

pyridine

pyridine

ظروف التفاعل

المعالجة

1. 1
   أخرىthe layers separated
2. 2
   غسيلThe aqueous layer was washed with additional DCM (2×15 ml)
3. 3
   أخرىdried (hydrophobic frit)
4. 4
   أخرىevaporated in vacuo
5. 5
   أخرىto give a brown oil
6. 6
   workup.ADDITIONwas added
7. 7
   استخلاص15 ml DCM to extract one more time
8. 8
   أخرىThe solvent was removed in vacuo

الإجراء التجريبي

To a stirred solution of 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (3 g, 12.00 mmol) in pyridine (12 ml), 2,4-difluorobenzenesulfonyl chloride (1.774 ml, 13.19 mmol) was added and the reaction mixture stirred at room temperature for 2 hours. 2 N HCl (aq) solution (20 ml) and DCM (20 ml) were added and the layers separated. The aqueous layer was washed with additional DCM (2×15 ml). Then the organic layers were combined, dried (hydrophobic frit) and evaporated in vacuo to give a brown oil. There was still some pyridine in the reaction mixture so 2M HCl was added and 15 ml DCM to extract one more time. The solvent was removed in vacuo to give the title compound as an orange solid (4.3 g).

المصدر