O-Phenylenediamine → HCID 58668628, compound

Participants

Reaction Conditions

Reaction Steps

N-(3-formyl-5-phenylpyridin-2-yl)-2,2-dimethylpropanamide (0.1 g, 0.35 mmol), o-phenylenediamine (0.038 g, 0.35 mmol), and NaHSO3 (0.039, 0.53 mmol) were combined in 3 mL of dimethylacetamide and heated to 250° C. in the SmithSynthesizer™ microwave instrument for 10 minutes. Upon cooling, the solvent was removed and the residue was chromatographed on silica gel eluting with hexanes/ethyl acetate (0 to 100% EtOAc over 20 minutes) to afford N-[3-(1H-benzimidazol-2-yl)-5-phenylpyridin-2-yl]-2,2-dimethylpropanamide (0.036 g). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.37 (s, 9H) 7.32 (m, 2H) 7.45 (m, 1H) 7.56 (t, J=7.60 Hz, 2H) 7.65 (d, J=7.87 Hz, 1H) 7.72 (d, J=7.87 Hz, 1H) 7.86 (dd, J=8.33, 1.19 Hz, 2H) 8.81 (d, J=10.07 Hz, 2H) 12.87 (s, 1H) 13.38 (s, 1H) MS m/z 371 (M+1)+.

Provenance & Evidence