Sodium Bicarbonate → HCID 89827138, compound

Participants

Reaction Conditions

Reaction Steps

4-Amino-8-bromocinnoline-3-carboxamide (0.040 g, 0.150 mmol), 2-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazole (0.048 g, 0.150 mmol), PdCl2(dppf) (5.48 mg, 7.50 μmol), dioxane (8 mL) and saturated NaHCO3 (2 mL) were combined and heated at 140° C. for 30 minutes in a microwave reactor. The reaction mixture was subsequently concentrated and purified via preparative HPLC (Phenomenex Gemini Prep 5 μm C18, 75×30 mm column) eluting with a gradient of 30-35% ACN/H2O (80/20 v/v, containing 10 mM NH4HCO3) in H2O (containing 10 mM NH4HCO3). The product-containing fractions were combined and acetonitrile was evaporated. The aqueous phase was diluted with saturated NaHCO3 and extracted with EtOAc. The organic phase was washed with water and the volatiles were evaporated to give the title compound as a light yellow solid (0.018 g, 32%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.47-7.65 (m, 4 H), 7.65-7.75 (m, 2 H), 7.83 (dd, J=8.21, 7.20 Hz, 1 H), 7.91-8.00 (m, 2 H), 8.23 (d, J=7.07 Hz, 2 H), 8.43 (d, J=7.58 Hz, 1 H), 8.54 (br s, 1 H); ESI-MS ma/z [(M+2H)/2]+ 191.1.

Provenance & Evidence