Cesium carbonate → HCID 66653612, compound

Participants

Reaction Conditions

Reaction Steps

1H-1,2,3-triazole (23 μL, 0.400 mmol, 2.00 eq.), copper (I) iodide (1.9 mg, 0.010 mmol, 0.05 eq.), cesium carbonate (130. mg, 0.400 mmol, 2.00 eq.) and N,N′-dimethyl-cyclohexane-1,2-diamine (7 μL, 0.040 mmol, 0.20 eq.) were added at r.t. to a solution of (±)-1-(5-bromo-2-ethoxycarbonylmethoxy-phenyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (105 mg, 0.200 mmol, 1.00 eq.) in DMF (0.1 mL) in a microwave tube. The tube was flushed with N2, sealed, and heated to 120° C. for 60 hours. The reaction mixture was diluted with water and washed with AcOEt. The remaining aqueous phase was acidified with 1N aq. HCl and extracted with AcOEt (3×). The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo. The crude residue, redissolved in DMF (1.2 mL), was purified by prep. HPLC (column: Atlantis, 19×50 mm, 5 um, UV/MS, acidic conditions) to give (±)-1-(2-carboxymethoxy-5-[1,2,3]triazol-1-yl-phenyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (LC-MS 1FA: tR=0.75 min; [M+H]+=485.2) and (±)-1-(2-carboxymethoxy-5-[1,2,3]triazol-2-yl-phenyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (LC-MS 1FA: tR=0.85 min; [M+H]+=485.1).

Provenance & Evidence