2-Trimethylsilylthiazole → HCID 68840249, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of n-BuLi (2.5M in hexane, 0.44 mL, 1.1 mmol) in Et2O (1 mL) at −78° C. is added 2-(trimethylsilyl)thiazole (0.16 mL, 1.0 mmol) and the reaction mixture is stirred at −78° C. for 30 min. Zinc chloride (1.0 M in Et2O1 3.0 mL, 3.0 mmol) is added and the mixture is warmed to RT over 30 min. The ether is removed under reduced pressure then a solution of 5-(2-benzyloxy-4-iodophenyl)-1,1-dioxo-2-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-3-one (250 mg, 0.46 mmol) and Pd(PPh3)4 (55 mg, 0.046 mmol) in THF (1 mL) is added. The yellow solution is stirred at RT for 1 h then is heated at reflux for 2 h. The mixture is quenched with 1N HCl, extracted with EtOAc, washed with brine, dried over MgSO4 and concentrated. The residue is purified by chromatography using EtOAc/hexane as eluent to afford the title compound as a yellow solid: 1H NMR (CDCl3) δ 0.01 (s, 9H), 0.83 (m, 2H), 3.51 (m, 2H), 4.33 (s, 2H), 5.13 (s, 2H), 7.27-7.37 (m, 6H) 7.48 (m, 2H), 7.73 (br s, 1H), 7.82 (d, J=4 Hz, 1H); (M+1)+=502.

Provenance & Evidence