TCMDC_ArylPyrrole

Problems with product decomposing before HRMS result. Query biological results.

See also Synthesis of amine-linked analogue of TCMDC-123812 via reductive amination using sodium cyanoborohydride in acidic conditions (AEW 12-1) and Synthesis of amine-linked analogue of TCMDC-123812 via reductive amination using sodium cyanoborohydride in acidic conditions (AEW 12-2)

Procedure:

AEW (100 mg, 0.46 mmol, 1 equiv) was dissolved in anhydrous MeOH (4 mL) and AcOH (0.15 mL) was added. Pyrrolidine (44 mg, 0.05 mL, 0.3 mmol, 1.3 equiv) in anhydrous MeOH (1 mL) was added and the reaction mixture stirred at room temperature for 1h. Sodium cyanoborohydride (32 mg, 0.52 mmol, 1.1 equiv.) was added in two portions over two minutes and the reaction mixture stirred at room temperature for 12 h. Then volatiles removed in vacuo, residue treated with aqueous 1 M NaOH and extracted with DCM (x2). Organics washed with brine, drieed and then filtered and evaporated to yield a crude orange oil (160 mg).

Hazard and Risk Assessment:

See Synthesis of amine-linked analogue of TCMDC-123812 via reductive amination using sodium cyanoborohydride in acidic conditions (AEW 12-1)