Triethylamine → 5-Bromobenzo[1,3]dioxole-4-carboxamide

Participants

Reaction Steps

Oxalyl chloride (6.13 mmol) was added to a solution of the acid (5-bromobenzo[1,3]dioxole-4-carboxylic acid) (3.25 mmol) in anhyd CH2Cl2 (30 ml) and the stirred mixture was refluxed for 2 h. Then the mixture was concentrated to dryness under reduced pressure. To this residue was added a solution of amine from step g (2.45 mmol) in anhyd CH2Cl2 (15 ml) and anhyd Et3N (3.67 mmol) and the mixture was stirred overnight at room temperature. The mixture was concentrated to dryness and diluted with CH2Cl2, then washed with 10% HCl, aq NaHCO3 solution and brine. The residue was dissolved in chloroform and subjected to flash chromatography to provide 5-bromobenzo[1,3]dioxole-4-carboxamide), N-(5-(biphenyl[1,1′]-4-yl)-6,7-dimethoxynaphthalen-1-yl) (1H NMR (CDCl3) δ 3.66 (s, 3H), 4.04 (s, 3H), 6.16 (s, 2H), 7.47-7.50 (m, 10H), 7.70-7-74 (m, 6H)).

Provenance & Evidence