Cesium carbonate → HCID 86677519, compound

Participants

Reaction Conditions

Reaction Steps

N-(3-(6-Chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)phenyl)acrylamide (50 mg, 0.130 mmol), 4-morpholinoaniline (23.22 mg, 0.130 mmol) and Cs2CO3 (42.4 mg, 0.130 mmol) were dissolved in toluene (4.5 mL) in a sealable microwave compatible reaction tube, and then Pd2(dba)3 (2.386 mg, 2.61 μmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (3.01 mg, 5.21 μmol) were added. The reaction tube was sealed and the reaction heated under microwave irradiation (30 min, 200° C., 3 atm). After completion of the reaction, the solvent was removed by vacuum and product was purified by flash column chromatography. 1H NMR (400 MHz, CD3OD): δ 8.64 (s, 1H), 8.28 (s, 1H), 7.93 (d, 1H, J=8.0 Hz), 7.72 (m, 3H), 7.50 (m, 1H), 6.96 (m, 2H), 6.43 (m, 2H), 5.90 (d, 1H, J=8.4 Hz), 5.80 (dd, 1H, J=2.8 and 8.8 Hz), 4.09 (m, 1H), 3.83 (m, 4H), 3.75 (m, 1H), 3.09 (m, 4H), 3.05 (m, 1H), 2.66 (m, 1H), 2.12 (m, 1H), 1.96 (m, 1H), 1.83-1.73 (m, 2H); ESI-MS: [M+H]+.

Provenance & Evidence