1-(2-fluorophenyl)butane-1,3-dione

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

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 100 mg (0.27 mmol) of Intermediate 45 and 58 mg (0.32 mmol) of Intermediate 20 to yield 55 mg of Example 37: TLC (EtOAc/MeOH (7:3): Rf=0.25; 1H NMR (DMSO-d6, 400 MHz) δ11.42 (d, 1H, J=8.93), 7.95 (m. 2H), 7.70 (dd, 1H, J=1.78, 7.69), 7.51 (m, 4H), 7.23 (m, 4H), 6.88 (d, 2H, J=8.50), 5.36 (s, 1H), 4.22 (m, 2H), 4.16 (brs, 1H), 3.18 (m, 1H), 2.94 (m, 2H), 2.84 (m, 1H), 2.40 (s, 3H), 1.70 (s, 3H); low resolution MS (ES−)m/e 545.1 (M-H); RP-HPLC (Vydac C-18, 25 cm×4.6 mm; 30-100% CH3CN in H2O) with 0.1% HCO2H buffer: 30 minutes; 1 mL/min: tr=19.47 min (to=1.43).

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 2′-fluoroacetophenone and 2.86 mL of EtOAc to yield Intermediate 20: 1H NMR (400 MHz, CDCl3, enol form) δ7.70 (dt, 1H. J=1.79, 7.69), 7.45 (m, 1H), 7.24 (m, 1H), 7.10 (m, 1H), 6.28 (s, 1H), 2.20 (s, 3H).

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 2′-fluoroacetophenone and 2.86 mL of EtOAc to yield Intermediate 20: 1H NMR (400 MHz, CDCl3, enol form) δ7.70 (dt, 1H. J=1.79, 7.69), 7.45 (m, 1H), 7.24 (m, 1H), 7.10 (m, 1H), 6.28 (s, 1H), 2.20 (s, 3H).