HCID 9974875, compound → HCID 68183245, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Z-3-(tributylstannyl)-2-propen-1-amine (30.0 g, 86.7 mmol) and 4-bromo-2-morpholin-4-yl-1,3-thiazole-5-carboxylate (27.8 g, 86.7 mmol) in toluene (136 mL) was purged with argon, and then tetrakis(triphenylphosphinepalladium(0) (5.01 g, 4.33 mmol) was added. The reaction mixture was stirred at 120° C. under an atmosphere of argon for 5 days. The solvent was evaporated, then the residue was adsorbed onto silica gel then purified using column chromatography on silica gel (600 gr Analogix column, gradient DCM to 5% MeOH in DCM over 40 minutes) to give the product (3.44 g, 16%). LCMS: (AA) ES+ 252. 1H NMR (400 MHz, d6-DMSO) δ: 7.73 (s, 1H), 6.63 (d, J=10.3 Hz, 1H), 6.24 (dt, J=10.3, 6.6 Hz, 1H), 3.74-3.63 (m, 4H), 3.54-3.47 (m, 2H), 3.47-3.40 (m, 4H).

Provenance & Evidence