Sodium Carbonate → HCID 178432499, compound

Participants

Reaction Steps

A mixture of 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1(e)) (50 mg, 0.21 mmol), 3-(trifluoromethyl)phenylboronic acid (Fluka) (55 mg, 0.287 mmol, 1.4 eq), tris(dibenzylideneacetone)dipalladium(0) (Aldrich Chemical Company) (4.7 mg, 0.0051 mmol, 0.025 eq) and triphenylphosphine (Aldrich Chemical Company) (10.8 mg, 0.041 mmol, 0.2 eq) in a mixed solvent (600 μL of toluene, 300 μL of 1.0 M Na2CO3, and 150 μL of ethanol) was heated at reflux under N2 for 19 h. Upon cooling to the room temperature, the reaction mixture was diluted with H2O (20 mL) and extracted with CHCl3 (3×20 mL). The organic phase was dried over Na2SO4, filtered, and concentrated with a rotary evaporator. Mp: 206-208° C. 1H NMR (CDCl3, 400 MHz): δ 8.58 (s, 1), 8.28 (s, 1), 8.18 (d, 1, J=7.6), 7.82 (d, 1, J=7.8), 7.77-7.72 (m, 3), 7.53 (t, 2, J=7.4), 7.46 (t, 1, J=7.4), 6.98(d, 1, J=2.0), 2.89 (s, 3). MS m/z: 354 (M+1), 352 (M−1).

Provenance & Evidence