Cesium carbonate → HCID 59373952, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (rac)-trans-3-(3-fluoropyrazin-2-yl)cyclohexanol (35 mg, 0.178 mmol), as prepared according to Scheme 35a, 4-(pyridin-2-ylamino)phenol (66.4 mg, 0.357 mmol), and cesium carbonate (116 mg, 0.357 mmol) in NMP (1 ml) was heated in a Biotage™ microwave reactor at 150° C. for 30 min. The mixture was partitioned between H2O (10 ml) and CH2Cl2 (20 ml), the layers were separated, and the aqueous layer was extracted with CH2Cl2 (3×20 ml). The combined organic layers were dried (MgSO4), concentrated under reduced pressure, and the resulting brown oil was purified by reversed phase HPLC (Gilson Gemini-NX 10u C18 110A, 100×50.0 mm, 10% to 95% H2O/MeCN, 0.1% TFA). The product containing fractions were combined, neutralized by the addition of solid Na2CO3, and extracted with CH2Cl2 (3×20 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to deliver (rac)-trans-3-(3-(4-(pyridin-2-ylamino)phenoxy)pyrazin-2-yl)cyclohexanol as a tan solid. MS (ESI, pos. ion) m/z: 363.0(M+1). IC50 (uM) 0.01049.

Provenance & Evidence