Isoamylamine → HCID 178422423, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 7-bromo-4-(bromoethynyl)-5-methyl-1-tosyl-1H-indole (35 mg, 0.075 mmol) and 3,4-diaminobenzonitrile (14.96 mg, 0.112 mmol) and DABCO (10.08 mg, 0.090 mmol) in NMP (0.3 mL) was stirred at 100° C. After stirring overnight the reaction mixture was loaded onto silica gel and was purified by flash chromatography (0-100% EtOAc in heptanes). The resulting residue was dissolved in EtOH (1.1 mL), KOH (51.8 mg, 0.924 mmol) and isoamylamine (0.21 mL, 1.85 mmol) were added, and the mixture was heated at 100° C. using microwave irradiation for 40 minutes. The resulting residue was purified directly by RP-HPLC (HC-A) to provide the title compound. 1H NMR (TFA salt, 400 MHz, DMSO-d6) δ ppm 11.22 (br. s., 1H) 7.97 (s, 1H) 7.59 (d, J=7.83 Hz, 1H) 7.51 (dd, J=8.21, 1.39 Hz, 1H) 7.33 (t, J=2.91 Hz, 1H) 7.21 (s, 1H) 6.55-6.66 (m, 1H) 4.47 (s, 2H) 2.38 (s, 3H). HRMS calcd. for C18H13BrN4 (M+H)+ 365.0396. found 365.0408.

Provenance & Evidence