1-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 86728292, compound

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of 5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-6-iodo-N-methylbenzofuran-3-carboxamide (100 mg, 0.16 mmol), 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (100 mg, 0.48 mmol) and K3PO4.3H2O (60 mg, 0.45 mmol) in DMF (2 mL) was added Pd(dppf)Cl2 (20 mg) under N2 protection. The reaction mixture was stirred at 100° C. for 16 hours. The mixture was filtered through a celite pad, and the resulting residue was concentrated to provide crude product. The resulting residue was purified using column chromatography (petroleum ether:EtOAc=1:2) to provide the product of Compound 165 (15 mg, yield: 16%). 1H-NMR (CDCl3, 400 MHz) δ 8.12 (s, 1H), 7.95 (dd, J=8.4, 6.0 Hz, 2H), 7.51 (s, 1H), 7.42 (s, 1H), 7.15 (t, J=8.8 Hz, 5H), 7.02 (d, J=8.0 Hz, 1H), 6.87 (d, J=8.4 Hz, 1H), 6.78 (t, J=8.8 Hz, 1H), 6.24 (s, 1H), 5.96 (s, 1H), 5.88 (s, 2H), 3.38 (s, 3H), 3.00 (d, J=5.2 Hz, 3H). MS (M+H)+: 588.

Provenance & Evidence