Sodium Carbonate → HCID 57502604, compound

Participants

Reaction Steps

A mixture of (D3) (1.0 eq) and pyridine-3-boronic acid (1.3 eq) in DMF (1.0 M) together with 2N Na2CO3 solution (2.0 eq) was degassed with a stream of Ar for 30 min. tBu3PH+BF4− (0.05 eq) and Pd2(dba)3 (0.05 eq) were added and the reaction mixture was heated at 90° for 48 h. The mixture was cooled to RT, DCM was added and the organic phase was washed with sat. aq. NaHCO3 solution, brine, dried (Na2SO4). The solution was concentrated under reduced pressure and the residue was purified by chromatography on silica gel eluting with 50-90% EtOAc/Petroleum ether then 10% MeOH/DCM to obtain the title compound as a yellow powder. 1H NMR (400 MHz, DMSO-d6, 300K) δ 9.40 (1H, s), 9.01 (1H, d, J=1.6 Hz), 8.63 (1H, dd, J=4.8, 1.6 Hz), 8.57 (1H, br. s), 8.32 (2H, d, J=8.8 Hz), 8.20 (1H, d, J=7.8 Hz), 8.10 (1H, br. s), 8.01 (2H, d, J=8.8 Hz), 7.88-7.82 (2H, m), 7.54 (1H, dd, J=7.8, 4.8 Hz). MS (ES) C19H13FN4O requires: 332. Found: 333 (M+H+).

Provenance & Evidence