4-(4-FLUOROPHENYL)-1,3-THIAZOLE-2-CARBALDEHYDE synthesis

Yield:383142-69-6 32.9%

Reaction Conditions:

Stage #1: 4-fluoroboronic acid;4-bromo-1,3-thiazole-2-carbaldehydewith caesium carbonate in 1,4-dioxane;water at 20; for 0.0833333 h;Suzuki Coupling;
Stage #2: with tetrakis(triphenylphosphine) palladium⁽⁰⁾ in 1,4-dioxane;water;Inert atmosphere;Reflux;

Steps:

1. Suzuki cross-coupling for the preparation of 4a-h, 7a-j and 10a-i

General procedure: Bromoarylaldehyde (1 mmol), aryl or alkenyl-boronicacid (1.2 mmol), and Cs₂CO₃(2.5 mmol) were dissolved orsuspended in a mixture of 1,4-dioxane (10 mL) and water (5 mL). The resulting mixture was stirred at RT for 5min. Tetrakis (triphenylphosphine) palladium(0) (0.05mmol) was added and the mixture was refluxed for 4-6 h under N₂ protection. After cooling to RT, the mixture was dilutedwith CH₂Cl₂ (10 mL) and the separated aqueous layer wasextracted with CH₂Cl₂ (3 × 10 mL). The combined organic layers were dried over Na₂SO₄,filtered, and the solution was concentrated in vacuo to obtain a residue, whichwas purified by silica gel CC using ethyl acetate-petroleum ether gradientelution (1:200-1:4, v/v) to afford the aldehydes.

References:

Zhang, Yang;Zhang, Zhuowei;Wang, Bo;Liu, Ling;Che, Yongsheng [Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,# 8,p. 1885 - 1888] Location in patent:supporting information