Water → HCID 69687024, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-trifluoromethanesulfonyloxy-naphthalene-1-carboxylic acid 2-trimethylsilanyl-ethyl ester (4.22 g, 10.0 mmol) in THF (40 mL) were added cesium carbonate (4.58 g, 14.05 mmol), palladium acetate (0.067 g, 0.3 mmol), BINAP (0.28 g, 0.45 mmol) and benzophenone imine (2.0 mL, 12.04 mmol) under an argon atmosphere. The mixture was heated at 65° C. for 16 h. After addition of water the mixture was extracted with EtOAc, washed with brine, dried (Na2SO4) and concentrated to dryness. To the residue were added THF (40 mL), methyl alcohol (10 mL) and 2N HCl (6.6 mL), and the mixture was stirred for 2 h at room temperature. After addition of 10% NaHCO3 the mixture was extracted, dried (Na2SO4) and concentrated to dryness. Purification by chromatography gave 1.8 g of 2-amino-naphthalene-1-carboxylic acid 2-trimethylsilanyl-ethyl ester.

Provenance & Evidence