methyl 3-phenyl-2-(trifluoromethylsulfonyloxy)propanoate

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: In a similar manner as described in step 1 of Example 7, the title compound was prepared from 6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthol (0.300 g, 0.676 mmol), prepared in step 2 of Example 11, 3-phenyl-2-trifluoromethanesulfonyloxypropionic acid methyl ester (0.317 g, 1.02 mmol) and cesium carbonate (0.441 g, 1.35 mmol) with the exception that this reaction was complete after 30 minutes at ambient temperature. Purification on a Biotage Horizon™ system with a KP-Sil Flash 25+M column (40 g Silica Gel, 60 Å) using 25% to 65% methylene chloride in hexane as the eluent gave methyl 2-{[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate as a white solid (0.257 g, 89%), mp 178–179° C. Elemental Analysis for C36H29NO3 Calc'd: C, 82.58; H, 5.58; N, 2.67. Found: C; 81.87; H, 5.10; N, 2.50. Purification on a Biotage Horizon™ system with a KP-Sil Flash 25+M column (40 g Silica Gel, 60 Å)

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

Procedure: In a similar manner as described in step 1 of Example 7, the title compound was prepared from 6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthol (0.300 g, 0.676 mmol), prepared in step 2 of Example 11, 3-phenyl-2-trifluoromethanesulfonyloxypropionic acid methyl ester (0.317 g, 1.02 mmol) and cesium carbonate (0.441 g, 1.35 mmol) with the exception that this reaction was complete after 30 minutes at ambient temperature. Purification on a Biotage Horizon™ system with a KP-Sil Flash 25+M column (40 g Silica Gel, 60 Å) using 25% to 65% methylene chloride in hexane as the eluent gave methyl 2-{[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate as a white solid (0.257 g, 89%), mp 178–179° C. Elemental Analysis for C36H29NO3 Calc'd: C, 82.58; H, 5.58; N, 2.67. Found: C; 81.87; H, 5.10; N, 2.50. Purification on a Biotage Horizon™ system with a KP-Sil Flash 25+M column (40 g Silica Gel, 60 Å)

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

Procedure: In a similar manner as described in step 1 of Example 7, the title compound was prepared from 6-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthol (0.300 g, 0.676 mmol), prepared in the previous step, 3-phenyl-2-trifluoromethanesulfonyloxypropionic acid methyl ester (0.317 g, 1.02 mmol) and cesium carbonate (0.441 g, 1.35 mmol). Purification on a Biotage Horizon™ system with a KP-Sil Flash 40+M column (100 g Silica Gel, 60 Å) using 25% to 65% methylene chloride in hexane as the eluent gave methyl 3-phenyl-2-[(6-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthyl)oxy]propanoate as an off-white amorphous solid (0.367 g, 90%), mp 50–55° C. Elemental Analysis for C38H30F3NO3 Calc'd: C, 75.36; H, 4.99; N, 2.31. Found: C, 75.24; H, 5.16; N, 2.22. Purification on a Biotage Horizon™ system with a KP-Sil Flash 40+M column (100 g Silica Gel, 60 Å)

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

Procedure: In a similar manner as described in step 6 of Example 1, the title compound was prepared from 6-(1-methyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthol (0.300 g, 1.00 mmol), prepared in step 2 of Example 5, 3-phenyl-2-trifluoromethanesulfonyloxypropionic acid methyl ester (0.469 g, 1.50 mmol) and cesium carbonate (0.653 g, 2.00 mmol) with the exception that this reaction was complete after 4 hours at ambient temperature. Purification on a Biotage Horizon™ system with a KP-Sil Flash 40+M column (100 g Silica Gel, 60 Å) using 25% to 55% methylene chloride in hexane as the eluent gave methyl 2-{[6-(1-methyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate as a white solid (0.437 g, 94%), mp 117–118° C. Elemental Analysis for C31H27NO3 Calc'd: C, 80.67; H, 5.90; N, 3.03. Found: C, 80.35; H, 6.16; N, 2.91. Purification on a Biotage Horizon™ system with a KP-Sil Flash 40+M column (100 g Silica Gel, 60 Å)

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

Procedure: In a similar manner as described in step 6 of Example 1, the title compound was prepared from 6-(1-methyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthol (0.300 g, 1.00 mmol), prepared in step 2 of Example 5, 3-phenyl-2-trifluoromethanesulfonyloxypropionic acid methyl ester (0.469 g, 1.50 mmol) and cesium carbonate (0.653 g, 2.00 mmol) with the exception that this reaction was complete after 4 hours at ambient temperature. Purification on a Biotage Horizon™ system with a KP-Sil Flash 40+M column (100 g Silica Gel, 60 Å) using 25% to 55% methylene chloride in hexane as the eluent gave methyl 2-{[6-(1-methyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate as a white solid (0.437 g, 94%), mp 117–118° C. Elemental Analysis for C31H27NO3 Calc'd: C, 80.67; H, 5.90; N, 3.03. Found: C, 80.35; H, 6.16; N, 2.91. Purification on a Biotage Horizon™ system with a KP-Sil Flash 40+M column (100 g Silica Gel, 60 Å)

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

Procedure: In a similar manner as described in step 6 of Example 1, the title compound was prepared from 6-(1-benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthol (0.140 g, 0.373 mmol), prepared in the previous step, 3-phenyl-2-trifluoromethanesulfonyloxypropionic acid methyl ester (0.175 g, 0.560 mmol) and cesium carbonate (0.243 g, 0.746 mmol). Purification on a Biotage FlashElute™ system with a KP-Sil Flash 40+M column (90 g Silica Gel, 60 Å) using 20% to 50% methylene chloride in hexane as the eluent gave methyl 2-{[6-(1-benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate as a white solid (0.175 g, 88%), mp 57–62° C. Elemental Analysis for C37H31NO3 Calc'd: C, 82.66; H, 5.81; N, 2.61. Found: C, 82.39; H, 5.88; N, 2.46. Purification on a Biotage FlashElute™ system with a KP-Sil Flash 40+M column (90 g Silica Gel, 60 Å)

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

Procedure: In a similar manner as described in step 6 of Example 1, the title compound was prepared from 6-(1-benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthol (0.140 g, 0.373 mmol), prepared in the previous step, 3-phenyl-2-trifluoromethanesulfonyloxypropionic acid methyl ester (0.175 g, 0.560 mmol) and cesium carbonate (0.243 g, 0.746 mmol). Purification on a Biotage FlashElute™ system with a KP-Sil Flash 40+M column (90 g Silica Gel, 60 Å) using 20% to 50% methylene chloride in hexane as the eluent gave methyl 2-{[6-(1-benzyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate as a white solid (0.175 g, 88%), mp 57–62° C. Elemental Analysis for C37H31NO3 Calc'd: C, 82.66; H, 5.81; N, 2.61. Found: C, 82.39; H, 5.88; N, 2.46. Purification on a Biotage FlashElute™ system with a KP-Sil Flash 40+M column (90 g Silica Gel, 60 Å)