8-bromo-2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene → HCID 66558840, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 12-bromo-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene (300 mg, 0.800 mmol), 1-isopropyl-4-(pyrrolidin-2-yl)piperidine hydrochloride (163 mg, 0.800 mmol), Pd(PtBu3)2 (20 mg, 0.040 mmol), Na2OtBu (232 mg, 2.40 mol) in toluene (2 mL) in a seal tube was degassed with N2 for three times. The resulting mixture was stirred at 110° C. for 120 min. After the completion of the reaction, the solid was filtered off via Celite. The filtrate was concentrated and purified by prep-HPLC (Gilson GX 281, Shim-pack PRC-ODS 250 mm×20 mm×2, gradient: CH3CN/10 mm/L NH4HCO3, 17 min) to give racemic 175 (40 mg, 10% yield). The (R) and (S) enantiomers were separated by chiral-HPLC (OD-H column, 10% IPA in hexane isocratic) to give 7.0 mg one enantiomer and 10 mg the other enantiomer.

Provenance & Evidence