Tris(furan-2-yl)phosphane → Tert-butyl cyclopropyl(2-(3-(trifluoromethoxy)phenyl)pyrazolo[1,5-a][1,3,5]triazin-4-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

Note: THF was degassed with a stream of N2 for 10 min. in a separate flask. Tert-butyl cyclopropyl(2-(methylthio)pyrazolo[1,5-a][1,3,5]triazin-4-yl)carbamate (100 mg, 0.31 mmol), 3-(trifluoromethoxy)phenyl boronic acid (154 mg, 0.74 mmol), tri(2-furyl)phosphine (86 mg, 0.37 mmol), copper(I) thiophene-2-carboxylate (167 mg, 0.88 mmol), Pd2 dba3 (24 mg, 0.03 mmol) were combined. The flask was evacuated and backfilled with N2. THF (3.7 mL) was added and the reaction was heated to 50° C. for 5 d. The solution was diluted with Et2O (40 mL) and washed with 10% NH4OH (3×30 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The solid residue was triturated with Et2O and filtered. The filtrate was concentrated in vacuo and purified via flash column chromatography (2.5-5% EtOAc/hexanes) to afford tert-butyl cyclopropyl(2-(3-(trifluoromethoxy)phenyl)pyrazolo[1,5-a][1,3,5]triazin-4-yl)carbamate (116 mg, 85%). LCMS (ES): >95% pure, m/z 436 [M+1]+.

Provenance & Evidence