TCMDC_ArylPyrrole

 

===

Synthesis of the ether-linked analogue of TCMDC-123812 from alcohol PMY 18-3 and 2-bromoacetamide using potassium carbonate as base.



Reaction Start Time: 16.25 12/03/12
PMY 18-3 (crude, 0.20 g, 0.91 mmol, 1 equiv.) was stirred in acetonitrile (10 mL) with potassium carbonate (252 mg, 1.82 mmol, 2.0 equiv.) 2-bromoacetamide (252 mg, 1.82 mmol, 2.0 equiv.) was added as a solid and the orange/brown mixture stirred at room temperature. After 16 hours, reaction showed minor products by TLC. Heated to 60 °C. After 3 hours, no change by TLC. Potassium iodide (332 mg, 2.00 mmol, 1.1 equiv. rel. alkylbromide) was added. After a further 1.5 hours, no change by TLC. A further portion of potassium iodide (332 mg, 2.00 mmol) was added followed by further 2-bromoacetamide (126 mg, 0.91 mmol, 1.0 equiv.). No change observed by TLC after a further 16 hours at 60 °C.

TLC (50% EtOAc/hexane) visualised with UV and vanillin:


Risk and Hazard Assessment:
As for: Synthesis of ether-linked analogue of TCMDC-123812 (PMY 37-1)

See also:
Synthesis of ether-linked analogues of TCMDC-123812 and TCMDC-123794 (PMY 19-1)
Synthesis of ether-linked analogue of TCMDC-123794 (PMY 17-2)
Synthesis of ether-linked analogue of TCMDC-123794 (PMY 17-1)