3-Nitrophenylboronic Acid → HCID 89629882, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (10 g, 65 mmol), 3-nitrophenylboronic acid (17.4 g, 104 mmol), Pd(dppf)Cl2—CH2Cl2 (2.13 g, 2.60 mmol), and 2 M sodium carbonate (81.5 mL, 163 mmol) in DMF (217 mL) was degassed for 10 minutes and then heated at 115° C. for 1 hour. After the reaction mixture was cooled to room temperature, water (700 mL) and sorbitol (20 g) were added which led to the precipitation of the desired product. After 30 minutes of stirring, the precipitate was filtered to give the crude product which was then slurried from EtOAc (100 mL) and hexanes (150 mL) for 30 minutes. Filtration of the precipitate gave 4-(3-nitrophenyl)-7H-pyrrolo[2,3-d]pyrimidine. LRMS (ESI) calc'd for C12H9N4O2 [M+H]+: 241, found 241.

Provenance & Evidence