Sodium Carbonate → HCID 22347123, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-ethanol (Intermediate 3) (0.120 g, 0.393 mmol), N1-[2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2-fluoro-4-(trifluoromethyl)benzamide (0.190 g, 0.433 mmol), palladium tetrakis(triphenylphosphine) (0.045 g, 0.039 mmol), and sodium carbonate (0.100 g, 0.943 mmol) in DME (3.9 mL) and water (3.9 mL) was heated at 85° C. for 3 h. The reaction mixture was cooled to ambient temperature and the organic solvent was removed in vacuo. The precipitate was collected by filtration, rinsed with water (20 mL) and ether (20 mL), and dried in vacuo to afford N1-{4-[4-amino-1-(2-hydroxyethyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-2-fluoro-4-(trifluoromethyl)benzamide as a brown solid (0.125 g, 0.254 mmol): 1H NMR (d6-DMSO, 400 MHz): δH 9.89 (1H, d, J=4.0 Hz), 8.31 (1H, d, J=8.0 Hz), 8.25 (1H, s), 7.99 (1H, t, J=7.4 Hz), 7.89 (1H, d, J=10.4 Hz), 7.75 (1H, d, J=8.0 Hz), 7.34 (1H, s), 7.31 (1H, d, J=8.4 Hz), 4.89 (1H, s), 4.40 (2H, t, J=5.6 Hz), 3.94 (3H, s), and 3.86 (2H, t, J=5.6 Hz); RP-HPLC (Hypersil C18, 5 μm, 100 Å, 15 cm; 5%-100% acetonitrile-0.1 M ammonium acetate over 15 min, 1 mL/min). Rt 9.85 min. MS: MH+ 491.

Provenance & Evidence