Benzaldehyde,2-(3-pyridinyl)-

Synthesis of (1E, 6E)-1-(4-hydroxyphenyl)-7-[2-(pyridin-3-yl)phenyl]hepta-1, 6-diene-3, 5-dione (CU513); (1) Synthesis of 2-(pyridin-3-yl)benzaldehyde; To a suspension of 1-bromobenzaldehyde (250 μL, 2.14 mmol), sodium carbonate (270 mg, 2.55 mmol), and 3-pyridineboronic acid (289 mg, 2.35 mmol) in 4.2 mL of N, N-dimethylformamide/water (2:1) were added palladium acetate (24 mg, 0.11 mmol) and triphenylphosphine (115 mg, 0.44 mmol) under nitrogen. After being stirred at 110°C overnight, the reaction mixture was filtered. The filtrate was diluted with chloroform, and the solution was washed with brine, and dried over MgSOGeneral procedure: In a 10-mL glass tube were placed halide (1.0mmol); 2-formylphenyl or 2-pyridyl MIDA boronate (1.5mmol) or allyl MIDA boronate; KTo Pd (PPh3) 4 (0.085g, 0. 07mmol) in acetonitrile (6mL), under nitrogen, was added water (2mL) followed by 2-formylphenylboronic acid (0. 55g, 3. 68mmol), 3-bromopyridine (0.36 mL, 3.68mmol) and potassium carbonate (2.69g, 22. 07mmol). After stirring for 3 days at 60C, the reaction mixture was purified by flash chromatography on silica, eluting with ethyl ACETATE/ISOHEXANE (10: 90 to 30: 70), to give the title compound as an oil. MS: [M+H] = 184.General procedure: In a 10-mL glass tube were placed halide (1.0mmol); 2-formylphenyl or 2-pyridyl MIDA boronate (1.5mmol) or allyl MIDA boronate; K2CO3 (3.0 mmol); Pd EnCat30(6mol%); and ethanol/H2O (4:1v/v) or water, and a magnetic stir bar. The vessel was sealed with a septum and placed into the microwave cavity. The temperature was ramped from rt to 120C or 135C. Once the reaction temperature was reached, the reaction mixture was held at this temperature for 10-18 min. After the mixture was allowed to cool to room temperature, the reaction vessel was opened and the contents were poured into a separating funnel. Water and ethylacetate (3×10mL) were added. The combined organics were dried over Na2SO4, filtered, and concentrated in vacuo. The organic residue was adsorbed onto silicagel, and then purified by column flash chromatography (hexane = ethyl acetate as eluent) to afford the desired product 1a-x. The biaryls, bipyridines, or allylphenols prepared are known compounds. [23-45] The products were confirmed by comparing the 1H NMR and mass spectral data with authentic samples reported in the literature.General procedure: To a mixture of benzaldehyde (20.1 mg, 0.2 mmol) and isopentyl amine (16 mg, 0.2 mmol) in 500 muL of DMF was added mercaptosuccinic acid (45 mg, 0.3 mmol) and the mixture was heated at 80 C for 16 h. The reaction mixture was cooled and partitioned between ethyl acetate and water. The organics were separated and dried and solvent removed to give the thiazoldinone acetic acid. The acid (31 mg, 0.1 mmol) was coupled with 3-(piperidin-4-yl)-3, 4-dihydroquinazolin-2(1H)-one (23 mg, 0.1 mmol) using HATU (38 mg, 0.1 mmol) in the presence of diisopropyl ethyl amine (44 muL, 0.25 mmol) in 300 muL of DMF at ambient temperature, and was purified with 10-90% acetonitrile/water to give 3-isopentyl-5-(2-oxo-2-(4-(2-oxo-1, 2-dihydroquinazolin-3(4H)-yl)piperidin-1-yl)ethyl)-2-phenylthiazolidin-4-one as the desired product.

Molecular Weight:183.21
XLogP3:1.9
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:183.068413911
Monoisotopic Mass:183.068413911
Topological Polar Surface Area:30
Heavy Atom Count:14
Complexity:193
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes