Cesium carbonate → HCID 66575773, compound

Participants

Reaction Conditions

Reaction Steps

(150 mg, 0.58 mmol) 2-Bromo-5-phenylethynyl-pyridine (Example 10, step 1) was dissolved in toluene (2 ml) and (RS)-tetrahydro-pyrrolo[1,2-b]pyrazol-2-one [CAS 1159091-93-6] (73 mg, 0.58 mmol, 1.0 equiv.), cesium carbonate (280 mg, 0.87 mmol, 1.5 equiv.), xantphos [CAS 161265-03-8] (14 mg, 0.02 mmol, 0.04 equiv.) and Pd2(dba)3 (11 mg, 0.01 mmol, 0.02 equiv.) were added under nitrogen. The mixture was stirred for 3 hours at 100° C. The crude product was purified by flash chromatography by directly loading the toluene mixture onto a silica gel column and eluting with an ethyl acetate:heptane gradient 0:100 to 100:0. The desired (RS)-1-(5-phenylethynyl-pyridin-2-yl)-tetrahydro-pyrrolo[1,2-b]pyrazol-2-one (17 mg, 9% yield) was obtained as a light brown solid, MS: m/e=304.1 (M+H+).

Provenance & Evidence