CHEMBRDG-BB 4015100

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

Procedure: Following a similar procedure to that described in reference example 3, but starting from 3-chloro-4-hydroxybenzaldehyde instead of 4-hydroxybenzaldehyde and using ethyl iodide instead of 2-iodopropane, the title compound of the example was obtained as an oil (98% yield).

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

Procedure: When the product of Step A was substituted for 3-chloro-4-ethoxybenzaldehyde in Example 49, Step A, the identical process afforded the title compound in 86% yield. 1H-NMR (DMSO-d6) 0.98 (tr, 3H, J=7.32 Hz); 1.68-1.79 (m, 2H); 4.06 (tr, 2H, J=6.39 Hz); 7.14 (d, 1H, J=8.7 Hz); 7.87 (dd, 1H, J=2.07, 8.61 Hz); 8.01 (d, 1H, J=2.04 Hz); 11.2 (broad s, 1H).

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

Procedure: When the product of Step A was substituted for 3-chloro-4-ethoxybenzaldehyde in Example 49 Step A the identical process afforded the title compound in 89% yield. 1H-NMR CDCl3) 1.4 (tr, 3H, J=6.95 Hz); 3.83 (s, 3H); 4.07 (q, 2H, J=6.96, 13.9, Hz); 6.79 (d, 1H, J=8.4 Hz); 7.47 (s, 1H); 7.58 (d, 1H, J=8.33 Hz).

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

Procedure: When the product of Step A was substituted for 3-chloro-4-ethoxybenzaldehyde in Example 49 Step A the identical process afforded the title compound in 89% yield. 1H-NMR CDCl3) 1.4 (tr, 3H, J=6.95 Hz); 3.83 (s, 3H); 4.07 (q, 2H, J=6.96, 13.9, Hz); 6.79 (d, 1H, J=8.4 Hz); 7.47 (s, 1H); 7.58 (d, 1H, J=8.33 Hz).

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

Procedure: When the product of Step A was substituted for 3-chloro-4-ethoxybenzaldehyde in Example 49, Step A the identical process afforded the title compound in 72% yield. 1H-NMR (CDCl3) 0.92 (tr, 3H); 1.42-1.65 (m, 4H); 1.76-1.9 (m, 2H); 4.08 (tr, 2H, J=6.51 Hz); 6.92 (d, 1H, J=8.7 Hz); 7.95 (dd, 1H, J=2.1, 8.61 Hz); 8.1 (d, 1H, J=2.07 Hz).

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

Procedure: When the product of Step A was substituted for 3-chloro-4-ethoxybenzaldehyde in Example 49, Step A the identical process afforded the title compound in 72% yield. 1H-NMR (CDCl3) 0.92 (tr, 3H); 1.42-1.65 (m, 4H); 1.76-1.9 (m, 2H); 4.08 (tr, 2H, J=6.51 Hz); 6.92 (d, 1H, J=8.7 Hz); 7.95 (dd, 1H, J=2.1, 8.61 Hz); 8.1 (d, 1H, J=2.07 Hz).

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

Procedure: When the product of Step A was substituted for 3-chloro-4-ethoxybenzaldehyde in Example 49, Step A the identical process afforded the title compound in 85% yield. 1H-NMR (CDCl3) 0.96 (tr, 3H, J=7.38 Hz); 1.46-1.57 (m, 2H); 1.59-2.77 (m, 2H); 4.1 (tr, 2H, J=6.45 Hz); 6.93 (d, 1H, J=8.67 Hz); 7.96 (dd, 1H, J=8.64, 2.1 Hz); 8.1 (d, 1H, J=2.07 Hz).

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

Procedure: When the 3-chloro-4-isopropoxybenzaldehyde was substituted for 3-chloro-4-ethoxybenzaldehyde in Example 49, Step A the identical process afforded the title compound in 98% yield, as a colourless solid. 1H-NMR (CDCl3) 1.4 (d, 6H, J=5.1 Hz); 4.67 (m, 1H); 6.95 (m, 1H); 7.96 (m, 1H); 8.10 (m, 1H).

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

Procedure: When the 3-chloro-4-isopropoxybenzaldehyde was substituted for 3-chloro-4-ethoxybenzaldehyde in Example 49, Step A the identical process afforded the title compound in 98% yield, as a colourless solid. 1H-NMR (CDCl3) 1.4 (d, 6H, J=5.1 Hz); 4.67 (m, 1H); 6.95 (m, 1H); 7.96 (m, 1H); 8.10 (m, 1H).

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

Procedure: When the product of Step B was substituted for 3-chloro-4-ethoxybenzaldehyde in Example 49, Step A the identical process afforded the title compound in 95% yield, as a colourless solid. 1H-NMR (CDCl3) 1.00 (tr, 3H, J=7.38 Hz); 1.73-1.87 (m, 2H); 3.98 (tr, 2H, J=6.47 Hz); 6.85 (d, 1H, J=8.65 Hz); 7.84 (dd, 1H, J=2.09, 8.68 Hz); 7.98 (d, 1H, J=2.07 Hz).

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

Procedure: When the product of Step B was substituted for 3-chloro-4-ethoxybenzaldehyde in Example 49, Step A the identical process afforded the title compound in 95% yield, as a colourless solid. 1H-NMR (CDCl3) 1.00 (tr, 3H, J=7.38 Hz); 1.73-1.87 (m, 2H); 3.98 (tr, 2H, J=6.47 Hz); 6.85 (d, 1H, J=8.65 Hz); 7.84 (dd, 1H, J=2.09, 8.68 Hz); 7.98 (d, 1H, J=2.07 Hz).

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

Procedure: Following a similar procedure to that described in reference example 3, but starting from 3-chloro-4-hydroxybenzaldehyde instead of 4-hydroxybenzaldehyde and using ethyl iodide instead of 2-iodopropane, the title compound of the example was obtained as an oil (98% yield).