Potassium Carbonate → HCID 52932050, compound

Participants

Reaction Steps

To a solution of 0.086 g (0.202 mmol) N-[(S)-(4-bromophenyl)(1-methyl-1H-1,2,3-triazol-4-yl)methyl]-2-(4-cyclopropylphenyl)acetamide in 1.0 ml THF was added 0.021 g (0.243 mmol) n-propylboronic acid, 0.017 g (0.020 mmol) PdCl2(dppf)-CH2Cl2 adduct, 0.084 g (0.607 mmol) solid potassium carbonate, and 0.117 g (0.607 mmol) Silver(I) oxide. The reaction mixture was irradiated in the microwave at 150° C. for 30 mins. The resulting solution was diluted with CH2Cl2, washed twice with water, dried over sodium sulfate, filtered, and concentrated in vacuo. Purification by preparative HPLC (5->95% CH3CN/H2O over 15 min, 0.05% added TFA, C18) to afford 0.024 g (30.6%) 2-(4-cyclopropylphenyl)-N-[(S)-(1-methyl-1H-1,2,3-triazol-4-yl)(4-propylphenyl)methyl]acetamide. 1H NMR (CDCl3, 400 MHz) 7.25 (m, 1H); 7.17-7.02 (m, 8H); 6.68 (d, J=8.24 Hz, 1H); 6.25 (d, J=7.78 Hz, 1H); 4.03 (s, 3H); 3.56 (s, 2H); 2.54 (t, J=7.42 Hz, 2H); 1.90-1.84 (m, 1H); 1.65-1.55-(m, 2H); 0.97-0.90 (m, 5H); 0.69-0.65 (m, 2H). HRMS (ES) [M+1]+ calcd for C24H28N4O: 389.2341. Found: 389.2343.

Provenance & Evidence