Sodium hydride → HCID 86620089, compound

Participants

Reaction Conditions

Reaction Steps

Into a 25 mL glass pressure tube fitted with Teflon screw cap and magnetic bar is placed 4-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)quinolin-7-yl]phenol (Example 7 before reverse phase HPLC purification); 0.100 g, 0.25 mmol), DMF (2 mL), trifluoro-methanesulfonic acid 2,2,2-trifluoroethyl ester (0.064 g 0.275 mmol), and 60% NaH (11 mg, 0.275 mmol). The cap is positioned, and mixture heated in oil bath at 70° C. for 16 h. The reaction is quenched with 15 mL water, giving 67 mg of precipitate as the title compound as a free base. The purified product, 36.4 mg (24%), is obtained by freeze drying appropriate fractions (based on MS analysis) from reverse phase HPLC using Waters Symmetry C18 column with a gradient of 10 to 70% B in A, where A is water containing 0.1% TFA and B is CH3CN containing 0.1% TFA.

Provenance & Evidence