Hydrochloric Acid → HCID 18932883, compound

Participants

Reaction Conditions

Reaction Steps

To 4-(6-chloro-2,3-dihydro-indol-1-yl)-quinazolin-7-ol (125 mg, 0.42 mmol; from Example 65) in DMF (2 mL) was added H2O (50 μL), K2 CO3 (s) (116 mg, 0.84 mmol), and tetramethylammonium hydroxide pentahydrate (15 mg, 0.08 mmol) followed by 2-bromoethyl methyl ether (43 μL, 0.46 mmol). The mixture was stirred at 50° C. under N2(g) for 24 hours before another aliquot (43 μL) of 2-bromoethyl methyl ether was added. Stirring at 50° C. was continued for another 36 hours before extractive workup and chromatography analogous to that described in Example 1 followed by conversion to the HCl salt as outlined for Example 2 afforded 91 mg (61%) of product. (M.P. 213°-216° C. (dec); LC-MS: 356 (MH+); anal. RP18-HPLC RT: 4.73 min.).

Provenance & Evidence