1,3-dichloro-2-prop-2-ynoxybenzene

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

Procedure: The title compound was prepared using analogous procedures described in EXAMPLE 3 from propyl (7-azido-6,7,8,9-tetrahydropyrido[1,2-α]indol-10-yl)acetate and 2,6-dichlorophenyl prop-2-yn-1-yl ether. 1H NMR (400 MHz, DMSO-d6): δ 12.14 (s, 1 H), 7.91 (s, 1 H), 7.54 (d, 2 H), 7.49 (d, 1 H), 7.35 (d, 1 H), 7.25 (t, 1 H), 7.11-7.00 (m, 2 H), 5.48-5.32 (m, 3 H), 4.78 (dd, 1 H), 4.37 (t, 1 H), 3.62 (d, 2 H), 3.43-3.34 (m, 1 H), 3.24-3.09 (m, 1 H), 3.09-2.97 (m, 1 H). MS (+ESI) m/z: 471.1.

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

Procedure: The title compound was prepared using analogous procedures described in EXAMPLE 3 from propyl (7-azido-6,7,8,9-tetrahydropyrido[1,2-α]indol-10-yl)acetate and 2,6-dichlorophenyl prop-2-yn-1-yl ether. 1H NMR (400 MHz, DMSO-d6): δ 12.14 (s, 1 H), 7.91 (s, 1 H), 7.54 (d, 2 H), 7.49 (d, 1 H), 7.35 (d, 1 H), 7.25 (t, 1 H), 7.11-7.00 (m, 2 H), 5.48-5.32 (m, 3 H), 4.78 (dd, 1 H), 4.37 (t, 1 H), 3.62 (d, 2 H), 3.43-3.34 (m, 1 H), 3.24-3.09 (m, 1 H), 3.09-2.97 (m, 1 H). MS (+ESI) m/z: 471.1.

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

Procedure: The title compound was prepared using analogous procedures described in EXAMPLE 3 from propyl (7-azido-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate and 2,6-dichlorophenyl prop-2-yn-1-yl ether. 1H NMR (400 MHz, DMSO-d6): δ 12.14 (s, 1H), 7.91 (s, 1H), 7.54 (d, 2H), 7.49 (d, 1H), 7.35 (d, 1H), 7.25 (t, 1H), 7.11-7.00 (m, 2H), 5.48-5.32 (m, 3H), 4.78 (dd, 1H), 4.37 (t, 1H), 3.62 (d, 2H), 3.43-3.34 (m, 1H), 3.24-3.09 (m, 1H), 3.09-2.97 (m, 1H). MS (+ESI) m/z: 471.1.

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

Procedure: The title compound was prepared using analogous procedures described in EXAMPLE 3 from propyl (7-azido-6,7,8,9-tetrahydropyrido[1,2-α]indol-10-yl)acetate and 2,6-dichlorophenyl prop-2-yn-1-yl ether. 1H NMR (400 MHz, DMSO-d6): δ 12.14 (s, 1 H), 7.91 (s, 1 H), 7.54 (d, 2 H), 7.49 (d, 1 H), 7.35 (d, 1 H), 7.25 (t, 1 H), 7.11-7.00 (m, 2 H), 5.48-5.32 (m, 3 H), 4.78 (dd, 1 H), 4.37 (t, 1 H), 3.62 (d, 2 H), 3.43-3.34 (m, 1 H), 3.24-3.09 (m, 1 H), 3.09-2.97 (m, 1 H). MS (+ESI) m/z: 471.1.