Heptane → HCID 11673096, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, a three neck round bottom flask is charged with 3-ethyl-2-methoxy-6-methyl-5-(4,4,5,5-tetramethyl-[1,3,2-dioxaborolan-2-yl)pyridine (7.8 g, 28.14 mmol) as prepared above, potassium carbonate (9.72 g, 70.33 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]-palladium dichloromethane (1.23 mg, 1.68 mmol) followed by anhyd dimethylformamide (100 mL). To this is added a solution of 2-bromothiophene (9.2 g, 56.44 mmol) in dimethylformamide (10 mL) and the resulting mixture is heated to 105-110° C. for 16 hr. The reaction is cooled, diluted with ethyl acetate and washed with water, with brine, dried (sodium sulfate), filtered and concentrated. The residue is purified by flash chromatography eluting with heptane, then heptane-5% ethyl acetate to afford 3-ethyl-2-methoxy-6-methyl-5-(thiophen-2-yl)pyridine as a yellow oil (94% yield).

Provenance & Evidence