Methanol → HCID 73335332, compound

Participants

Reaction Conditions

Reaction Steps

The carbinol obtained above (69 mg, 0.4 mmol) was diluted in 1.2 mL of THF and 500 μL of DMF and treated with K2CO3 (111 mg, 0.8 mmol) and 2-chloro-1-(1-(4-fluorophenyl)-6,7-dihydro-1H-pyrazolo[4,3-b]pyridin-4(5H)-yl)ethanone (118 mg, 0.4 mmol). The slurry was heated to 75° C. The reaction slurry was diluted with EtOAc and washed with brine, dried on MgSO4, filtered, and concentrated. The residue was purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to provide 69 mg of the desired product (43%) as a white solid. 1H NMR (400 MHz, CDCl3, mixture of rotamers) δ 8.37 (s, 0.8H), 7.63 (s, 0.2H), 7.42-7.46 (m, 2H), 7.13-7.19 (m, 2H), 5.14 (s, 0.4H), 5.03 (s, 1.6H), 3.90 (m, 0.4H), 3.87 (m, 1.6H), 2.86 (m, 2H), 2.28 (s, 2.4H), 2.25 (s, 0.6H), 2.05-2.13 (m, 2H), 1.62 (s, 6H); MS: (ES) m/z calculated for C21H24ClFN5O2 [M+H]+ 432.2, found 432.1.

Provenance & Evidence