Pyridine → HCID 86701783, compound

Participants

Reaction Steps

To (±)-2-(1-(tert-butoxycarbonyl)-5-methoxy-7-methyl-1H-indol-4-yl)-2-methylpent-4-enoic acid (Example 156-D) (0.76 g, 2.035 mmol) in DCM (20.35 mL) was added DMF (7.88 μl, 0.102 mmol) and then oxalyl chloride (0.356 ml, 4.07 mmol). After 20 minutes the reaction was concentrated in vacuo. The crude product in THF (5 mL) was added to a mixture of 3,4-diaminobenzonitrile (0.48 g, 3.60 mmol) in THF (5 mL) and pyridine (0.494 ml, 6.11 mmol) at 0° C. After 10 minutes the reaction was stirred at room temperature. After 30 minutes the reaction was heated at 55° C. for 4 hours. At this point the volatiles were removed in vacuo and the crude product was absorbed onto silica to purify via FCC (0-50% EtOAc:heptanes) to obtain the title compound. MS (ESI+) m/z 489.5 (M+H).

Provenance & Evidence