1-ethynyl-3-fluorobenzene

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

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

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

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

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 titled compound was prepared according to Method CB using the product of Example 83D (79 mg, 0.5 mmol) and 1-ethynyl-3-fluorobenzene (Aldrich, 60 mg, 0.5 mmol). 1H NMR (300 MHz, MeOH-d4) δ 7.19-7.33 (m, 1H), 7.48 (s, 1 H), 7.58 (td, J=8.1, 5.8 Hz, 1H), 7.69 (dt, J=9.6, 2.2 Hz, 1H), 7.77 (dt, J=8.0, 1.1 Hz, 1H), 8.70 (d, J=2.4 Hz, 1H), 8.76 (dd, J=2.4, 1.7 Hz, 1H), 9.29 (d, J=1.4 Hz, 1H) ppm; MS (DCI/NH3) m/z 242 (M+H)+.

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

Procedure: The titled compound was prepared as the hydrochloride salt according to Method CB using the product of Example 44B (79 mg, 0.5 mmol) and 1-ethynyl-3-fluorobenzene (Aldrich, 60 mg, 0.5 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.35-7.51 (m, 1H), 7.67 (td, J=8.1, 5.9 Hz, 1H), 7.73-7.82 (m, 2H), 7.86 (s, 1H), 9.32 (s, 2H), 9.36 (s, 1H) ppm; MS (DCI/NH3) m/z 242 (M+H)+.

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

Procedure: The titled compound was prepared according to Method CB using the product of Example 28B (88 mg, 0.5 mmol) and 1-ethynyl-3-fluorobenzene (Aldrich, 60 mg, 0.5 mmol). 1H NMR (300 MHz, MeOH-d4) δ 7.20-7.35 (m, 1H), 7.46 (s, 1 H), 7.58 (td, J=8.0, 5.8 Hz, 1H), 7.68 (ddd, J=9.7, 2.5, 1.7 Hz, 1H), 7.76 (dt, J=8.0, 1.1 Hz, 1H), 8.17 (ddd, J=9.4, 2.8, 1.7 Hz, 1H), 8.61 (d, J=2.7 Hz, 1H), 8.97 (t, J=1.5 Hz, 1H) ppm; MS (DCI/NH3) m/z 259 (M+H)+.

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

Procedure: The titled compound was prepared as the hydrochloride salt according to Method CB using the product of Example 1A (78 mg, 0.5 mmol) and 1-ethynyl-3-fluorobenzene (Aldrich, 60 mg, 0.5 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.35-7.51 (m, 1H), 7.60-7.82 (m, 4H), 7.84 (s, 1H), 8.42 (dt, J=8.1, 1.7 Hz, 1H), 8.80 (dd, J=5.0, 1.4 Hz, 1H), 9.17 (d, J=1.6 Hz, 1H) ppm; MS (DCI/NH3) m/z 241 (M+H)+.

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

Procedure: Following protocol H, 1-Ethynyl-3-fluoro-benzene was treated with n-BuLi, CF3CO2Et and BF3—OEt2 in THF. Reaction with hydrazine in benzene under similar reaction conditions yielded title compound. under similar reaction conditions

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

Procedure: Following protocol H, 1-Ethynyl-3-fluoro-benzene was treated with n-BuLi, CF3CO2Et and BF3—OEt2 in THF. Reaction with hydrazine in benzene under similar reaction conditions yielded title compound. under similar reaction conditions