Methanol → N,N-Dimethyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazol-1-yl]-piperidine hydrochloride (253.6 mg, 0.809 mmol, 1 eq) in DMF (6 mL), DIPEA (0.7 mL, 4 mmol, 5 eq) was added at rt. The solution was cooled to 0° C. and N,N-dimethylcarbamoyl chloride (107.7 mg, 1.002 mmol, 1.2 eq) in DMF (1 mL) was added. The reaction was stirred from 0° C.→rt for 30 min. MeOH was added and all organic solvent was concentrated in vacuo to dryness. The residue was dissolved in CH2Cl2, washed with water (1×) and brine (1×), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo, giving 292.5 mg (98%, 0.798 mmol) of the title compound, as a waxy white solid that had solidified upon drying. 1H NMR (400 MHz, CDCl3): δ=1.32 (s, 12H), 1.94-2.07 (m, 2H), 2.16 (dd, J=12.3, 2.4 Hz, 2H), 2.85 (s, 6H), 2.87-2.95 (m, 2H), 3.78 (d, J=13.4 Hz, 2H), 4.24-4.34 (m, 1H), 7.76 (s, 1H), 7.80 (s, 1H). MS (AP+): m/z=349.13 (100) [MH+]. HPLC: tR=2.91 min (ZQ3, polar—5 min).

Provenance & Evidence