Sodium Azide → HCID 18932816, compound

Participants

Reaction Conditions

Reaction Steps

To 1-(6,7-dimethoxy-quinazolin-4-yl)-2,3-dihydro-1H-indol-6-ylamine (104 mg, 0.323 mmol; from Example 30) in 80% acetic acid/H2O (8 mL) was added NaNO2 (35 mg, 0.35 mmol) in H2O(200 μL) at 5° C. After stirring 10 min. at 5° C. a solution of NaN3 (22mg, 0.34 mmol) in H2O(200 μL) was added and the mixture was allowed to warm to 22° C. and stirred for 1 hour. Following the removal of solvents by lyophilization the residue was dissolved in EtOAc and washed with saturated aqueous NaHCO3 (2×), and brine, and the organic phase was dried over MgSO4(s), filtered and concentrated in vacuo. The residue was chromatographed on silica (2% MeOH/CHCl3) to afford 72 mg of the azide. (M.P. 184°-186° C. (dec); LC-MS: 349 (MH+); anal. RP18-HPLC RT: 4.70 min.).

Provenance & Evidence