2-(Tri-n-butylstannyl)oxazole → 5-Oxazol-2-yl-thiophene-3-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

5-Bromo-thiophene-3-carboxylic acid methyl ester (0.3 g, 1.35 mmol) was dissolved in toluene (5 mL), 2-tributylstannyl oxazole (0.311 mL, 1.48 mmol) was added then the reaction mixture was purged with nitrogen before addition of palladium tetrakis(triphenylphosphine) (0.14 g, 0.12 mmol). The reaction mixture was heated at 100° C. over the weekend. The mixture was filtered then evaporated and the residue was purified by chromatography on a silica II cartridge, eluting with 10-20% DCM in pentane to give the title compound as a yellow solid (0.105 g). LCMS m/z 210 [M+H]+ and 251.23 [M+MeCN+H]+ R.T.=3.03 min (Analytical Method 6).

Provenance & Evidence