1-ethynyl-3,5-difluorobenzene

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 69B (57 mg, 0.3 mmol) and 1-ethynyl-3,5-difluorobenzene (Apollo, 41 mg, 0.3 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.51 (tt, J=9.3, 2.4 Hz, 1 H), 7.61-7.74 (m, 2H), 7.93 (s, 1H), 8.41 (t, J=2.1 Hz, 1H), 8.82 (d, J=2.4 Hz, 1 H), 9.06 (d, J=1.7 Hz, 1H) ppm; MS (DCI/NH3) m/z 293 (M+H)+, 295 (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-3,5-difluorobenzene (Apollo, 69 mg, 0.5 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.52 (tt, J=9.5, 2.4 Hz, 1H), 7.62-7.78 (m, 2H), 7.93 (s, 1H), 9.30 (s, 2H), 9.36 (s, 1H) ppm; MS (DCI/NH3) m/z 260 (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-3,5-difluorobenzene (Apollo, 69 mg, 0.5 mmol). 1H NMR (300 MHz, MeOH-d4) 87.16 (tt, J=9.1, 2.2 Hz, 1H), 7.53 (s, 1H), 7.54-7.63 (m, 2H), 8.17 (ddd, J=9.1, 2.8, 1.6 Hz, 1H), 8.62 (d, J=2.8 Hz, 1H), 8.97 (t, J=1.6 Hz, 1H) ppm; MS (DCI/NH3) m/z 277 (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-3,5-difluorobenzene (Apollo, 69 mg, 0.5 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.50 (tt, J=9.3, 2.4 Hz, 1H), 7.60-7.78 (m, 3H), 7.89 (s, 1H), 8.32 (dt, J=7.8, 2.2 Hz, 1H), 8.76 (d, J=3.4 Hz, 1H), 9.11 (d, J=1.7 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: Prepared as described for 3,4-bis(benzyloxy)-6-(phenylethynyl)pyridazine (Intermediate 2) from 3,4-bis(benzyloxy)-6-chloropyridazine (Intermediate 1) and 1-ethynyl-3,5-difluorobenzene. Prepared

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 69B (57 mg, 0.3 mmol) and 1-ethynyl-3,5-difluorobenzene (Apollo, 41 mg, 0.3 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.51 (tt, J=9.3, 2.4 Hz, 1 H), 7.61-7.74 (m, 2H), 7.93 (s, 1H), 8.41 (t, J=2.1 Hz, 1H), 8.82 (d, J=2.4 Hz, 1 H), 9.06 (d, J=1.7 Hz, 1H) ppm; MS (DCI/NH3) m/z 293 (M+H)+, 295 (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-3,5-difluorobenzene (Apollo, 69 mg, 0.5 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.52 (tt, J=9.5, 2.4 Hz, 1H), 7.62-7.78 (m, 2H), 7.93 (s, 1H), 9.30 (s, 2H), 9.36 (s, 1H) ppm; MS (DCI/NH3) m/z 260 (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-3,5-difluorobenzene (Apollo, 69 mg, 0.5 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.52 (tt, J=9.5, 2.4 Hz, 1H), 7.62-7.78 (m, 2H), 7.93 (s, 1H), 9.30 (s, 2H), 9.36 (s, 1H) ppm; MS (DCI/NH3) m/z 260 (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-3,5-difluorobenzene (Apollo, 69 mg, 0.5 mmol). 1H NMR (300 MHz, MeOH-d4) 87.16 (tt, J=9.1, 2.2 Hz, 1H), 7.53 (s, 1H), 7.54-7.63 (m, 2H), 8.17 (ddd, J=9.1, 2.8, 1.6 Hz, 1H), 8.62 (d, J=2.8 Hz, 1H), 8.97 (t, J=1.6 Hz, 1H) ppm; MS (DCI/NH3) m/z 277 (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-3,5-difluorobenzene (Apollo, 69 mg, 0.5 mmol). 1H NMR (300 MHz, MeOH-d4) 87.16 (tt, J=9.1, 2.2 Hz, 1H), 7.53 (s, 1H), 7.54-7.63 (m, 2H), 8.17 (ddd, J=9.1, 2.8, 1.6 Hz, 1H), 8.62 (d, J=2.8 Hz, 1H), 8.97 (t, J=1.6 Hz, 1H) ppm; MS (DCI/NH3) m/z 277 (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-3,5-difluorobenzene (Apollo, 69 mg, 0.5 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.50 (tt, J=9.3, 2.4 Hz, 1H), 7.60-7.78 (m, 3H), 7.89 (s, 1H), 8.32 (dt, J=7.8, 2.2 Hz, 1H), 8.76 (d, J=3.4 Hz, 1H), 9.11 (d, J=1.7 Hz, 1H) ppm; MS (DCI/NH3) m/z 259 (M+H)+.