Sodium Azide → HCID 66665358, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.69 g (1.703 mmol) [5-(5-bromo-2-fluoro-phenyl)-5-fluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl]-carbamic acid tert-butyl ester and 72.7 mg (0.511 mmol) trans-N,N′-dimethylcyclohexane-1,2-diamine in 7.5 ml EtOH was added a solution of 443 mg (6.81 mmol) sodium azide and 67.5 g (0.341 mmol) sodium-ascorbate in 3 ml water. The mixture was degassed and brought under nitrogen atmosphere. CuI (64.9 mg, 0.341 mmol) was added and the mixture was heated at 70° C. The initially formed suspension turned into a homogeneous blue solution. The mixture was cooled to rt, diluted with water and TBME. The organic phase was washed with brine and dried with MgSO4.H2O. The crude product, consisting of a mixture of aryl azide and aniline, was dissolved in 3 ml EtOH and 3 ml THF and treated with 20 mg 10% Pd—C and stirred under an atmosphere of hydrogen until all azide had been consumed. The mixture was diluted with DCM and filtered over celite. The product was purified by chromatography on silica gel (heptane/30% EtOAc) to give the desired product as colorless foam.

Provenance & Evidence