Bicarbonate Ion → (E)-5-(2-fluoro-1,2-di(pyridin-4-yl)vinyl)-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-ethynyl-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (138 mg, 0.6 mmol), 4-bromopyridinehydrochloride (100 mg, 0.51 mmol), dichlorobistriphenyl phosphine palladium (II) (10 mg, 0.015 mmol) and TBAF.3H2O (481 mg, 1.5 mmol) were added to a reaction vessel and the contents heated at 80° C. (exothermicity observed; temperature 140° C.) for 5 min in microwave. After completion of the reaction (as monitored by TLC & LCMS) reaction mixture was poured into water (20 mL) and saturated bicarbonate solution was added. The desired compound was extracted with EtOAc (3×20 mL). The organic layer was washed with water (2×20 mL), dried over sodium sulfate and concentrated under vacuum to obtain crude product which was purified by reverse phase HPLC. 1H NMR (CDCl3, TFA salt) δ (ppm): 8.60 (d, 2H), 8.22 (d, 2H), 7.35 (d, 2H), 7.06 (s, 1H), 6.90 (d, 2H), 6.70 (d, 2H), 4.30 (m, 2H), 3.60 (m, 1H), 3.46 (m, 2H), 3.10 (m, 1H), 2.90 (s, 3H), 2.30 (s, 3H).

Provenance & Evidence