Hydrochloric Acid → Methyl 3-aminoisoquinoline-8-carboxylate

Participants

Reaction Conditions

Reaction Steps

A 20 mL microwave vial was charged with methyl 3-chloroisoquinoline-8-carboxylate (0.56 g, 2.57 mmol), [1,1′-biphenyl]-2-yldicyclohexylphosphine (90 mg, 0.257 mmol), LHMDS (3.0 mL, 3.08 mmol) and Pd2(dba)3 (118 mg, 0.125 mmol) and then with 12 mL of THF. Reaction mixture was capped and stirred at 65° C. overnight. Then 2M HCl (1.2 mL, 2.57 mmol) was added and stirred at rt for 20 min. The reaction mixture was filtered and added with sat bi carb. Extracted with EtOAc. Combined organic layer was dried, filtered, concentrated in vacuo. Purified by silica gel chromatography (0-50% EtOAc in hexane) yielded 90% Methyl 3-aminoisoquinoline-8-carboxylate (27-2).

Provenance & Evidence