4-Methylpiperidine → HCID 58754821, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1.00 g (7.09 mmol) of 1-fluoro-2-nitro-benzene in DMF (5 mL) was treated with 2.52 mL (21.3 mmol) of 4-methyl-piperidine and heated to 60° C. for 15 min. The mixture was diluted with EtOAc (50 mL) and washed with water (6×30 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. A 250 mg (1.14 mmol) portion of the residue was taken up in THF (5 mL) and treated with 15 mg of 10% Pd/C (Degussa type E101-NE/W, Aldrich, 50% by weight water) under H2 (1 atm). When this reaction was complete, the mixture was filtered through Celite directly into a suspension of 24.5 mg (0.147 mmol) of PyBroP, 30.0 mg (0.0980 mmol) of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylate potassium salt (as prepared in Example 11, step (d)), and 51.0 μL (0.295 mmol) of DIEA in THF (5 mL). The mixture was flushed with Ar and stirred at RT for 16 h. An additional 24.5 mg (0.147 mmol) of PyBroP, 30.0 mg (0.0980 mmol) of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylate potassium salt (as prepared in Example 11, step (d)), and 51.0 μL (0.295 mmol) of DIEA were added, and the mixture stirred for 2 h. The mixture was diluted with EtOAc (10 mL), washed with water (1×10 mL) and saturated aqueous NaHCO3 (1×10 mL), dried (MgSO4), and concentrated in vacuo to afford 153 mg (30%) of the title compound as a white solid: Mass spectrum (ESI, m/z): Calcd. for C23H33N5Si, 440.2 (M+H), found 440.0.

Provenance & Evidence