反应详情

To a solution of 4-(7-Benzenesulfonyl-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (150 mg, 0.29 mmol) in 4 mL DME (degassed with nitrogen prior to use) was added 0.94M aqueous Na2CO3 (0.61 mL, 0.57 mmol) and Pd(PPh3)4 (66 mg, 0.057 mmol). The reaction mixture was stirred 5 minutes, then 2-thiophene boronic acid (55 mg, 0.43 mmol) was added. The reaction mixture heated to reflux and stirred 16 hours, after which it was cooled to room temperature and DME was removed by rotary evaporation. The reaction mixture was diluted with H2O and extracted with DCM, and the combined extracts were dried (Na2SO4), filtered, and concentrated. The crude was purified on silica gel (8:1 to 4:1 hexanes:EtOAc) to furnish 4-(7-Benzenesulfonyl-5-thiophen-2-yl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (120 mg, 79%) as a beige powder. LCMS (APCI+) m/z 526 [M+H]+; Rt: 3.25 min.

1. temperatureThe reaction mixture heated
2. temperatureto reflux
3. stirringstirred 16 hours
4. customDME was removed by rotary evaporation
5. additionThe reaction mixture was diluted with H2O
6. extractionextracted with DCM
7. dry with materialthe combined extracts were dried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customThe crude was purified on silica gel (8:1 to 4:1 hexanes:EtOAc)