تفاعل #67124

معادلة التفاعل

6-Bromo-1-(phenylsulfonyl)-4-[5-(tetrahydro-1,4-oxazepin-4(5H)-ylmethyl)-1,3,4-oxadiazol-2-yl]-1H-indazole

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

potassium phosphate tribasic

water

→

N-(2-(Methyloxy)-5-{1-(phenylsulfonyl)-4-[5-(tetrahydro-1,4-oxazepin-4(5H)-ylmethyl)-1,3,4-oxadiazol-2-yl]-1H-indazol-6-yl}-3-pyridinyl)methanesulfonamide

المذيبات

1,4-dioxane

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONhalf of the resulting solution was charged to a reaction vessel
2. 2
   غسيلwashing with MeOH
3. 3
   أخرىThe solvent was removed under a stream of nitrogen
4. 4
   أخرىthe residue was partitioned between DCM (10 ml) and water (10 ml)
5. 5
   أخرىseparated with a hydrophobic frit
6. 6
   أخرىthe solvent again removed under a stream of nitrogen
7. 7
   أخرىThe residue was purified by preparative HPLC

الإجراء التجريبي

6-Bromo-1-(phenylsulfonyl)-4-[5-(tetrahydro-1,4-oxazepin-4(5H)-ylmethyl)-1,3,4-oxadiazol-2-yl]-1H-indazole (279 mg, 0.538 mmol) was dissolved in 1,4-dioxane (5 ml) and half of the resulting solution was charged to a reaction vessel. N-[2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]methanesulfonamide (114 mg, 0.347 mmol), 1,1′-bis(diphenylphosphino)ferrocene palladium dichloride (39.5 mg, 0.054 mmol), potassium phosphate tribasic (171.5 mg, 0.808 mmol) and water (0.25 ml) were added. The reaction mixture was heated at 100° C. for 20 mins. The mixture was passed through a 1 g silica SPE cartridge, washing with MeOH. The solvent was removed under a stream of nitrogen and the residue was partitioned between DCM (10 ml) and water (10 ml), separated with a hydrophobic frit and the solvent again removed under a stream of nitrogen. The residue was purified by preparative HPLC using the following method:

المصدر