Pyridine → HCID 69687430, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-amino-naphthalene-1-carboxylic acid 2-trimethylsilanyl-ethyl ester (604 mg, 2.1 mmol) in toluene (12 mL) were added pyridine (0.34 mL, 4.21 mmol) and 20% phosgene in toluene (1.58 mL, 3.04 mmol) under a nitrogen atmosphere. The mixture was heated at 90° C. for 1.5 h, cooled to room temperature and filtered. The filtrate was concentrated to dryness. To the residue were added toluene (12 mL), (5-phenyl-benzofuran-2-yl)-methanol (471 mg, 2.10 mmol) and 4-dimethylaminopyridine (26 mg, 0.21 mmol) under a nitrogen atmosphere, and the mixture was heated at 90° C. for 16 h. Following dilution with EtOAc, the mixture was washed with 2N HCl, 10% NaHCO3, and brine, dried (Na2SO4) and concentrated to dryness. Purification by chromatography gave 582 mg of 2-(5-phenyl-benzofuran-2-ylmethoxycarbonylamino)-naphthalene-1-carboxylic acid 2-trimethylsilanyl-ethyl ester.

Provenance & Evidence