Tetramethyltin → 5-(5-chloro-benzo[1,3]dioxol-4-yl)-6-cyano-7-methyl-4-oxo-4,5-dihydro-3H-1-thia-3,5,8-triaza-acenaphthylene-2-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

7-chloro-5-(5-chloro-benzo[1,3]dioxol-4-yl)-6-cyano-4-oxo-4,5-dihydro-3H-1-thia-3,5,8-triaza-acenaphthylene-2-carboxylic acid ethyl ester Compound 1g (115 mg, 0.242 mmol) was combined with 95% tetramethyltin (0.039 ml, 0.266 mmol), PdCl2(Ph3P)2 (17 mg, 0.024 mmol) and DMF (3 mL) in a sealed microwave vessel. The mixture was heated to 150° C. for 15 mins. The reaction mixture was diluted with 0.5 M NaH2PO4 and extracted with EtOAc, then dried (MgSO4) and evaporated. The resulting residue was purified by flash chromatography (30 to 50% EtOAc/hexane/1% Et3N) to give 5-(5-chloro-benzo[1,3]dioxol-4-yl)-6-cyano-7-methyl-4-oxo-4,5-dihydro-3H-1-thia-3,5,8-triaza-acenaphthylene-2-carboxylic acid ethyl ester Compound 2a (57 mg) as a white solid. LC/MS 457 (MH+).

Provenance & Evidence