Diisopropylethylamine → HCID 178489062, compound

Participants

Reaction Steps

To (±)-2-(1-(tert-butoxycarbonyl)-5-methoxy-7-methyl-1H-indol-4-yl)-2-cyanopropanoic acid (Example 155-E) (1.4 g, 3.91 mmol) in DCM (39.1 ml) at 0° C. was added DIPEA (2.05 ml, 11.72 mmol) followed by HBTU (1.926 g, 5.08 mmol) and 4-bromobenzene-1,2-diamine (1.096 g, 5.86 mmol) at 0° C. and stirred in the ice bath for 20 minutes. The ice bath was removed and the reaction was stirred at room temperature overnight. The reaction was diluted with water, the layers were separated and the organic layer was dried over Na2SO4 and concentrated. The residue was dissolved in acetic acid (7 mL) and heated at 85° C. for 4 hours. The reaction was cooled to 0° C. and quenched with a saturated solution of sodium bicarbonate, diluted with water and EtOAc. The layers were separated and the organic layer was removed, dried over Na2SO4 and concentrated. The crude product was purified via FCC (0-50% EtOAc:heptanes) to obtain the title compound. MS (ESI+) m/z 409.3, 411.3 (M+H).

Provenance & Evidence