5-ethynyl-1,2,3-trifluorobenzene

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 5-ethynyl-1,2,3-trifluorobenzene (Apollo, 78 mg, 0.5 mmol). 1H NMR (300 MHz, MeOH-d4) δ 7.53 (s, 1H), 7.79 (dd, J=8.5, 6.4 Hz, 2H), 8.70 (d, J=2.4 Hz, 1H), 8.76 (dd, J=2.5, 1.5 Hz, 1H), 9.29 (d, J=1.7 Hz, 1H) ppm; MS (DCI/NH3) m/z 278 (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 69B (57 mg, 0.3 mmol) and 5-ethynyl-1,2,3-trifluorobenzene (Apollo, 47 mg, 0.3 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.87 (s, 1H), 7.92 (dd, J=8.6, 6.6 Hz, 2H), 8.39 (t, J=2.0 Hz, 1H), 8.82 (d, J=2.4 Hz, 1H), 9.04 (d, J=1.7 Hz, 1H) ppm; MS (DCI/NH3) m/z 311 (M+H)+, 313 (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 5-ethynyl-1,2,3-trifluorobenzene (Apollo, 78 mg, 0.5 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.88 (s, 1H), 7.95 (dd, J=8.6, 6.6 Hz, 2H), 9.29 (s, 2H), 9.36 (s, 1H) ppm; MS (DCI/NH3) m/z 278 (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 5-ethynyl-1,2,3-trifluorobenzene (Apollo, 78 mg, 0.5 mmol). 1H NMR (300 MHz, MeOH-d4) δ 7.49 (s, 1H), 7.76 (dd, J=8.3, 6.6 Hz, 2H), 0.16 (ddd, J=9.2, 2.7, 1.7 Hz, 1H), 8.62 (d, J=2.7 Hz, 1H), 8.95 (t, J=1.5 Hz, 1H) ppm; MS (DCI/NH3) m/z 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 1A (78 mg, 0.5 mmol) and 5-ethynyl-1,2,3-trifluorobenzene (Apollo, 78 mg, 0.5 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.69 (dd, J=7.9, 4.8 Hz, 1H), 7.85 (s, 1H), 7.95 (dd, J=8.7, 6.7 Hz, 2H), 8.35 (dt, J=8.1, 1.7 Hz, 1H), 8.79 (d, J=3.6 Hz, 1H), 9.11 (s, 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 83D (79 mg, 0.5 mmol) and 5-ethynyl-1,2,3-trifluorobenzene (Apollo, 78 mg, 0.5 mmol). 1H NMR (300 MHz, MeOH-d4) δ 7.53 (s, 1H), 7.79 (dd, J=8.5, 6.4 Hz, 2H), 8.70 (d, J=2.4 Hz, 1H), 8.76 (dd, J=2.5, 1.5 Hz, 1H), 9.29 (d, J=1.7 Hz, 1H) ppm; MS (DCI/NH3) m/z 278 (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 69B (57 mg, 0.3 mmol) and 5-ethynyl-1,2,3-trifluorobenzene (Apollo, 47 mg, 0.3 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.87 (s, 1H), 7.92 (dd, J=8.6, 6.6 Hz, 2H), 8.39 (t, J=2.0 Hz, 1H), 8.82 (d, J=2.4 Hz, 1H), 9.04 (d, J=1.7 Hz, 1H) ppm; MS (DCI/NH3) m/z 311 (M+H)+, 313 (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 69B (57 mg, 0.3 mmol) and 5-ethynyl-1,2,3-trifluorobenzene (Apollo, 47 mg, 0.3 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.87 (s, 1H), 7.92 (dd, J=8.6, 6.6 Hz, 2H), 8.39 (t, J=2.0 Hz, 1H), 8.82 (d, J=2.4 Hz, 1H), 9.04 (d, J=1.7 Hz, 1H) ppm; MS (DCI/NH3) m/z 311 (M+H)+, 313 (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 5-ethynyl-1,2,3-trifluorobenzene (Apollo, 78 mg, 0.5 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.88 (s, 1H), 7.95 (dd, J=8.6, 6.6 Hz, 2H), 9.29 (s, 2H), 9.36 (s, 1H) ppm; MS (DCI/NH3) m/z 278 (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 5-ethynyl-1,2,3-trifluorobenzene (Apollo, 78 mg, 0.5 mmol). 1H NMR (300 MHz, MeOH-d4) δ 7.49 (s, 1H), 7.76 (dd, J=8.3, 6.6 Hz, 2H), 0.16 (ddd, J=9.2, 2.7, 1.7 Hz, 1H), 8.62 (d, J=2.7 Hz, 1H), 8.95 (t, J=1.5 Hz, 1H) ppm; MS (DCI/NH3) m/z 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 1A (78 mg, 0.5 mmol) and 5-ethynyl-1,2,3-trifluorobenzene (Apollo, 78 mg, 0.5 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.69 (dd, J=7.9, 4.8 Hz, 1H), 7.85 (s, 1H), 7.95 (dd, J=8.7, 6.7 Hz, 2H), 8.35 (dt, J=8.1, 1.7 Hz, 1H), 8.79 (d, J=3.6 Hz, 1H), 9.11 (s, 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 5-ethynyl-1,2,3-trifluorobenzene (Apollo, 78 mg, 0.5 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.69 (dd, J=7.9, 4.8 Hz, 1H), 7.85 (s, 1H), 7.95 (dd, J=8.7, 6.7 Hz, 2H), 8.35 (dt, J=8.1, 1.7 Hz, 1H), 8.79 (d, J=3.6 Hz, 1H), 9.11 (s, 1H) ppm; MS (DCI/NH3) m/z 277 (M+H)+.