Sodium Carbonate → 1,1-dimethylethyl 5-(4-amino-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2,3-dihydro-1H-indole-1-carboxylate

온도

120 °C

To a 25 mL pressure tube was charged 3-bromo-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (670 mg, 2.94 mmol), 1,1-dimethylethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-indole-1-carboxylate (1014 mg, 2.94 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (120 mg, 0.147 mmol), and sodium carbonate (494 mg, 5.88 mmol) followed by dioxane (8 mL), and water (2 mL). The reaction was heated at 120° C. for 40 minutes in a microwave reactor. LCMS showed no more SM. The reaction was cooled to room temperature, the mixture was transferred into a 100 mL Erlenmeyer flask, rinsed by EtOAc, with the water layer and black greasy solid stayed in tube (total 50 mL of EtOAc was added to the mixture). White solid was formed in brown solution. The solid was filtered to give titled product (764 mg).

1. temperatureThe reaction was cooled to room temperature
2. washrinsed by EtOAc, with the water layer and black greasy solid
3. customstayed in tube
4. addition(total 50 mL of EtOAc was added to the mixture)
5. customWhite solid was formed in brown solution
6. filtrationThe solid was filtered

ORD 기록

ord-3357db5901bb498fb3391804defe49e4

출처 데이터셋

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08598156B2