Potassium Iodide → HCID 59649707, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 3-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenol (0.15 g, 0.85 mmol) (from Example 7 supra), potassium carbonate (0.25 g, 1.8 mmol) and 18-Crown-6 (10 mg, 0.04 mmol) (Aldrich) in N,N-dimethylformamide (5 mL) was heated at 65° C. in a sealed tube with magnetic stirring for 2 hours. 3-Bromomethyl-4-chloro-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (0.27 g, 0.8 mmol) (from Example 1 supra) and potassium iodide (0.13 g, 0.8 mmol) were then added and mixture heated at 65° C. in the sealed tube for another 20 hours. After cooling, mixture was partitioned between ethyl acetate (2×100 mL) and water (2×100 mL). Organic layers were washed with brine, then combined, dried (MgSO4), filtered and concentrated. Residue was purified by flash chromatography (Biotage 40S, 20% ethyl acetate in dichloromethane as solvent) to give 4-chloro-3-[3-(5-methyl-[1,3,4]oxadiazol-2-yl)-phenoxymethyl]-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester as a white powder. (Yield 0.22 g, 63.1%).

Provenance & Evidence