Dimethylformamide → 5-(5-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

6-Methoxy-1,3-benzothiazole (0.136 g, 0.82 mmol; M. A. Matulenko et al. Bioorg. Med. Chem. 2005, 13, 3705.) and 6-bromo-N,N-dimethylpyridin-3-amine (0.199 g, 0.99 mmol) were reacted according to the procedure used for the preparation of 6-methoxy-2-[5-(trifluoromethyl)pyridin-2-yl]-1,3-benzothiazole, with the following exceptions: 10 mol % bis(tri-t-butylphosphine) palladium (0) was used, the amount of DMF was reduced (2 mL) and the reaction mixture was heated at 150° C. for 4.5 h before it was filtered through a short plug of silica that was rinsed by DCM and DMF. The solvents were evaporated under reduced pressure and the residue was subjected to flash chromatography (Heptane/EtOAc gradient). The title compound (0.100 g) was isolated as a yellow solid. 1H NMR (CHLOROFORM-d) δ 8.19-8.15 (m, 2H) 7.90 (d, 1H) 7.38 (d, 1H) 7.09-7.04 (m, 2H) 3.90 (s, 3H) 3.10 (s, 6H); MS m/z (M+H) 286.

Provenance & Evidence