Sodium Carbonate → HCID 67520735, compound

Participants

Reaction Conditions

Reaction Steps

Into the DCM (5 ml) solution of 4-{4-[6-amino-5-(7-methoxyisoquinolin-3-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (101 mg, 0.171 mmol), cooled in an ice/water bath, was added 1.00 M of boron tribromide in DCM (2.0 ml) over 5 min. The mixture was stirred at 0° C. and warmed to rt overnight. After that time, the mixture was basified with saturated Na2CO3 until pH 10 and extracted with EtOAc (3×30 ml). The extracts were washed with brine (2×20 ml), dried over MgSO4, filtered and concentrated in vacuo, giving the title compound as a light-yellow solid. 1H NMR (400 MHz, CD3OD): δ=1.90-2.02 (m, 2H), 2.09-2.18 (m, 2H), 2.74-2.82 (m, 2H), 3.18-3.24 (m, 2H), 4.26-4.36 (m, 1H), 7.27 (d, J=2.4 Hz, 1H), 7.36 (dd, J=2.4 & 9.2 Hz, 1H), 7.84-7.87 (m, 2H), 8.06 (d, J=0.8 Hz, 1H), 8.07 (d, J=3.2 Hz, 1H), 8.10 (s, 1H), 8.17 (d, J=2.4 Hz, 1H), 9.08 (s, 1H). MS(ES+): m/z=387.14 (100) [MH+]. HPLC: tR=0.66 & 1.85 min (ZQ3, polar—5 min; peak splitting).

Provenance & Evidence