1-(4-methylphenyl)butane-1,3-dione

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: first using 1-(4-methylphenyl)-1,3-butanedione to prepare 3-(4-methylphenyl)-1-methyl-3-oxo-1-propenamine.

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared (as described above for the preparation of Example 2) from 790 mg (1.64 mmol) of Intermediate 45 (as the TFA salt) and 0.29 g (1.64 mmol) of Intermediate 27 (with 660 μL of DCA replacing Et3N) to yield crude product contaminated with DCA). A second silica gel chromatography column eluting with 8:1 DCM:MeOH gave 70 mg of Example 19 as a beige-colored solid: TLC (DCM/MeOH (4:1): Rf=0.58; 1H NMR (DMSO-d6, 400 MHz) δ11.43 (d, 1H, J=9.0), 7.96 (m, 2H), 7.74 (d, 2H, J=8.1), 7.54 (m, 3H), 7.24 (d, 2H, J=8.1), 7.18 (d, 2H, J=8.4), 6.87 (d, 2H, J=8.4), 5.57 (s, 1H), 4.21 (t, 2H, J=6.6), 4.08 (m, 1H), 3.23 (m, 2H), 2.95 (t, 2H, J=6.6), 2.80(dd, 1H, J=13.8, 9.0), 2.39 (s, 3H), 2.37 (s, 3H), 1.71 (s, 3H); low resolution MS (ES+)m/e 525.2 (MH+). to yield crude product A second silica gel chromatography column eluting with 8:1 DCM

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared (as described above for Intermediate 16) from 2.0 g of 4′-methylacetophenone and 2.9 mL of EtOAc to yield 1.68 grams of Intermediate 27: TLC analysis: Rf=0.61 (5/1, hexanes/EtOAc), 1H NMR (400 MHz, CDCl3, enol form) δ7.72 (d, 2H, J=8.2), 7.24 (d, 2H, J=7.4), 6.15 (s, 1H), 2.4 (s, 3H), 2.2 (s, 3H).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: first using 1-(4-methylphenyl)-1,3-butanedione to prepare 3-(4-methylphenyl)-1-methyl-3-oxo-1-propenamine.