Cesium fluoride → HCID 136378660, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of PdCl2(PPh3)2 (10 mg; 0.01 mmol; 0.11 eq.), tert-butyl 5-[(3-chloro-6-oxopyridazin-1(6H)-yl)methyl]-3-{1-[4-(morpholin-4-ylcarbonyl)phenyl]-1H-1,2,3-triazol-4-yl}-1H-indazole-1-carboxylate (79 mg; 0.13 mmol; 1.0 eq.), 4-hydroxyphenylboronic acid (35 mg; 0.25 mmol; 2.0 eq.) and cesium fluoride (65 mg; 0.43 mmol; 3.3 eq.) in DMF (2.0 mL) and water (1.0 mL) was degassed with argon in a sealed tube and heated in MW at 120° C. for 1.5 h. The mixture was then filtered through a celite pad. The filtrate was diluted with EtOAc. The phases were separated and organic phase was washed with a 1 N solution of HCl, dried over magnesium sulfate, filtered and concentrated. Purification of the crude by preparative HPLC gave the title compound as a white solid (9 mg, 9%). 1H NMR (300 MHz, DMSO-d6) δ 13.40 (s, 1H), 9.85 (br, 1H), 9.38 (s, 1H), 8.46 (s, 1H), 8.18-8.12 (m, 2H), 7.98 (d, J=9.8 Hz, 1H), 7.76 (d, J=8.7 Hz, 2H), 7.69 (d, J=8.6 Hz, 2H), 7.59 (d, J=8.6 Hz, 1H), 7.54-7.46 (m, 1H), 7.05 (d, J=9.7 Hz, 1H), 6.85 (d, J=8.7 Hz, 2H), 5.46 (s, 2H), 3.75-3.43 (m, 8H). HPLC (max plot) 98.6%; Rt 3.14 min. UPLC/MS: (MS+) 575.1, (MS−) 573.0.

Provenance & Evidence