Sodium Carbonate → HCID 58585765, compound

Participants

Reaction Conditions

Reaction Steps

The mixture of 4-chloro-3-cyano-quinoline-6-carboxylic acid ethyl ester (example 46c, 1.3 g, 5 mmol), (2-methylpropyl)boronic acid (1.0 g, 10 mmol), sodium carbonate (3.18 g, 30 mmol) and POPd (bis[bis(1,1-dimethylethyl)phosphinous acid-κP]dichloropalladium, CAS: 391683-95-7) (75 mg, 0.15 mmol) in dimethyloxyethane (DME) (20 mL) was stirred at 100° C. for 2 days. After cooling to room temperature, the product was extracted with ethylacetate. The combined organic layers were successively washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 0%-50% ethyl acetate in hexanes in 30 min) afforded 3-cyano-4-isobutyl-quinoline-6-carboxylic acid ethyl ester (1.1 g, 79%) as a clear oil. LC-MS m/e 283 (MH+).

Provenance & Evidence