Benzo(B)Thiophene-2-Boronic Acid → HCID 25019426, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of sodium carbonate hydrate (250 mg, 2016 μmol), PdCl2(dppf)-CH2Cl2 adduct (30 mg, 37 μmol), 6-chloro-2-(2-(7-methoxyquinolin-4-yloxy)ethyl)pyridazin-3(2 H)-one (220 mg, 663 μmol), and benzo[b]thiophen-2-ylboronic acid (290 mg, 1629 μmol) in DME (5 mL) and H2O (2 mL) was heated to 80° C. under nitrogen for 18 h. The mixture was cooled to room temperature and partitioned between EtOAc (50 mL) and H2O (20 mL). The organic phase was washed with H2O (2×), NH4Cl (aq), dried over Na2SO4, and concentrated to a brown solid. The solid was triturated with hot hexane-EtOAc-MeOH (2:1:0.1) twice and the solid was further washed with MeOH in EtOAc (1%), CH2Cl2 (de-colorization), and ether to give the product as an off-white solid (160 mg). MS (ESI pos. ion) calc'd for C24H19N3O3S: 429.11; found 430.2 (MH+). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.65 (s, 3 H) 5.46 (s, 4 H) 7.76 (d, J=4.11 Hz, 1 H) 7.81 (d, J=9.19 Hz, 1 H) 7.95 (d, J=9.39 Hz, 1 H) 8.08 (s, 1 H) 8.24 (d, J=3.33 Hz, 2 H) 8.67 (d, J=5.09 Hz, 1 H) 8.81 (d, J=8.41 Hz, 2 H) 8.88 (s, 1 H) 9.00 (d, J=9.78 Hz, 1 H) 9.44 (d, J=4.30 Hz, 1 H)

Provenance & Evidence