Cesium carbonate → HCID 4435389, compound

Participants

Reaction Conditions

Reaction Steps

2-Iodopyrazine (2.00 g, 9.42 mmol), copper(I) iodide (366 mg, 1.88 mmol), cesium carbonate (6.14 g, 18.84 mmol), 4-hydroxybenzonitrile (1.68 g, 14.13 mmol) and N,N-dimethylglycine hydrochloride (398 mg, 2.83 mmol) were dried and placed under nitrogen and then degassed 1,4-dioxane (25.0 mL) was added. The whole mixture was heated at 90° C. for 138 hours. The cooled mixture was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2×50 mL). The organic layers were combined and washed with brine (50 mL) and dried with Na2SO4 and concentrated in vacuo. The crude solid was placed on a silica gel column and purified (EtOAc/Hex 1:8) to give the product as an off white solid (1.61 g, 87%). 1H NMR (300 MHz, CDCL3) δ(ppm): 7.31 (2H, d, J=9.1 Hz), 7.74 (2H, d, J=9.1 Hz), 8.14 (1H, dd, J=2.4, 1.4 Hz), 8.37 (1H, d, J=2.4 Hz), 8.51 (1H, s). 13C NMR (75 MHz, CDCL3) δ(ppm): 109.0, 118.5, 122.0 (CH), 134.1 (CH), 136.4 (CH), 139.8 (CH), 141.1 (CH), 156.7, 159.1. MS (FAB+): 198 (MH+). HRMS for C11H7N3O (MH+): calculated: 198.0667; found 198.0661.

Provenance & Evidence