2-Methyl-2-butene → (2-(4-Methylthiazol-2-ylamino)pyridin-4-yloxy)phenol

Participants

Reaction Conditions

Reaction Steps

A 50 mL round bottom flask was charged with 4-(2-methoxyphenoxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine (6.38 mL, 0.638 mmol) and dichloromethane (6 mL). The solution was cooled to 0° C., and tribromoborane (0.181 mL, 1.91 mmol) and 1 mL of 2-methyl-2-butene were added. The reaction mixture was stirred at 0° C. for 1 hour. Water and saturated solution of NaHCO3 were added, and the reaction mixture was extracted with EtOAc. The organic layer was dried over magnesium sulfate, filtered and concentrated. The residue was purified on a prepacked silica gel column, eluting with 20-35% EtOAc in hexanes to give 2-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)phenol (0.130 g, 67.4% yield) as light yellow solid. 1H NMR (DMSO) δ 10.90 (bs, 1H), 9.70 (bs, 1H), 8.10 (d, 1H), 7.11 (m, 2H), 7.01 (dd, 1H), 6.87 (dt, 1H), 6.49 (d, 1H), 6.43 (m, 2H), 2.19 (d, 3H); Mass spectrum (esi) m/z=300 (100) (M+H).

Provenance & Evidence