تفاعل #1000556
ord-d8eda18189e14ab6aa9884dda324a3be
معادلة التفاعل
الكواشف
ظروف التفاعل
المعالجة
- 1درجة الحرارةThe mixture was warmed until a solution
- 2أخرىwas obtained
- 3غسيلto rinse the vial
- 4أخرىThe vial was capped
- 5أخرىThe reaction was quenched
- 6workup.ADDITIONby adding the reaction mixture drop-wise to water (60 ml)
- 7أخرىA precipitate formed
- 8ترشيحThe solid was collected by vacuum filtration
- 9workup.DISSOLUTIONThe solid was then dissolved in methanol
- 10أخرىadsorbed onto silica gel (6 g) for purification by HPFC (0-15% CMA in chloroform, 1440 mL)
- 11تركيزconcentrated
- 12أخرىthe resulting solid was recrystallized from methanol
- 13أخرىto provide a peach colored crystalline solid, mp 218-220° C
الإجراء التجريبي
A scintillation vial was charged with 4-amino-2-ethylthiazolo[4,5-c]quinolin-7-ol (1.0 eq., 1.0 mmol) and anhydrous DMF (2 mL). The mixture was warmed until a solution was obtained. An additional amount of DMF (1 mL) was added. To this stirred orange solution was added cesium carbonate (3.0 eq., 3.0 mmol) and a solution of 3-(2-bromoethyl)indole (1.0 eq., 1.0 mmol) dissolved in DMF (2 mL). Additional DMF (1 mL) was used to rinse the vial. The vial was capped and heated to 60° C. overnight. The reaction was monitored by HPLC. The reaction was quenched by adding the reaction mixture drop-wise to water (60 ml) with stirring. A precipitate formed. The solid was collected by vacuum filtration. The solid was then dissolved in methanol and adsorbed onto silica gel (6 g) for purification by HPFC (0-15% CMA in chloroform, 1440 mL). Pure fractions were combined and concentrated; the resulting solid was recrystallized from methanol to provide a peach colored crystalline solid, mp 218-220° C. MS (APCI) m/z 389 (M+H)+. Anal. calcd for C22H20N4OS.0.8 CH3OH: C, 66.13; H, 5.65; N, 13.53. Found: C, 66.43; H, 5.03; N, 13.90.