N-Methyl-1-(2-methyl-2,3-dihydro-1H-isoindol-5-yl)methanamine → HCID 46176238, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 5-({[(4-methoxy-2,6-dimethylphenyl)sulfonyl](methyl)amino}methyl)-1,3,4-oxadiazole-2-carboxylate (30 mg, 0.081 mmol) and N-methyl-1-(2-methyl-2,3-dihydro-1H-isoindol-5-yl)methanamine (29 mg, 0.162 mmol) were dissolved in DCE (5 mL) and stirred at 0° C. prior to being degassed with N2. Trimethylaluminium (2M in toluene, 80 μl) was added dropwise to this solution. Upon completion of addition, the reaction was heated to 60° C. and stirred for 1 h. The reaction was cooled, and saturated aqueous NaHCO3 (10 mL) was added. The aqueous layer was extracted with DCM (3×10 mL) and the combined organic extracts dried over Na2SO4 and concentrated in vacuo. The resulting brown oil was purified by FCC, eluting with 99:1 DCM:7M NH3 in MeOH followed by purification using prep method D to afford the title compound.

Provenance & Evidence