1-(chloromethyl)-4-(trifluoromethoxy)benzene

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: The procedure of Example 87 is repeated using 1.8 g of p-thiocresol and 9.6 g of 4-(trifluoromethoxy)benzyl chloride. This affords 10.9 g of the desired product as white crystals.

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

Procedure: The procedure of Example 87 is repeated using 1.8 g of p-thiocresol and 9.6 g of 4-(trifluoromethoxy)benzyl chloride. This affords 10.9 g of the desired product as white crystals.

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

Procedure: The procedure of Example 87 is repeated using 11.8 g of p-thiocresol and 9.6 g of 4-(trifluoromethoxy)benzyl chloride. This affords 10.9 g of the desired product as white crystals.

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

Procedure: To a solution of 2-(2-Fluoro-phenyl)-1H-pyrrolo[3,2-c]pyridine (50 mg, 0.244 mmole) in DMF (1 ml) was added 10% (w/v) aqueous NaOH (113 μl, 0.28 mmole) followed by a solution of 4-trifluoromethoxybenzyl chloride (60 mg, 0.28 mmole) in DMF (0.5 ml). The reaction mixture was stirred at room temperature for 1 hour. The crude reaction mixture was purified by reverse phase HPLC with mass directed collection. Obtained 87 mg (74%) of 2-(2-Fluoro-phenyl)-5-(4-trifluoromethoxy-benzyl)-5H-pyrrolo[3,2-c]pyridinium trifluoroacetate. The crude reaction mixture was purified by reverse phase HPLC with mass collection

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

Procedure: To a solution of 2-(2-Fluoro-phenyl)-1H-pyrrolo[3,2-c]pyridine (50 mg, 0.244 mmole) in DMF (1 ml) was added 10% (w/v) aqueous NaOH (113 μl, 0.28 mmole) followed by a solution of 4-trifluoromethoxybenzyl chloride (60 mg, 0.28 mmole) in DMF (0.5 ml). The reaction mixture was stirred at room temperature for 1 hour. The crude reaction mixture was purified by reverse phase HPLC with mass directed collection. Obtained 87 mg (74%) of 2-(2-Fluoro-phenyl)-5-(4-trifluoromethoxy-benzyl)-5H-pyrrolo[3,2-c]pyridinium trifluoroacetate. The crude reaction mixture was purified by reverse phase HPLC with mass collection

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

Procedure: To a solution of 2-(2-Fluoro-phenyl)-1H-pyrrolo[2,3-c]pyridine (50 mg, 0.244 mmole) in DMF (1 ml) was added 10% (w/v) aqueous NaOH (113 μl, 0.28 mmole) followed by a solution of 4-trifluoromethoxybenzyl chloride (60 mg, 0.28 mmole) in DMF (0.5 ml). The reaction mixture was stirred at room temperature for 1 hour. The crude reaction mixture was purified by reverse phase HPLC with mass directed collection. Obtained 9.2 mg (8%) of 2-(2-Fluoro phenyl)-6-(4-trifluoromethoxy-benzyl)-6H-pyrrolo[2,3-c]pyridinium trifluoroacetate after repurification. The crude reaction mixture was purified by reverse phase HPLC with mass collection

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

Procedure: The procedure of Example 87 is repeated using 11.8 g of p-thiocresol and 9.6 g of 4-(trifluoromethoxy)benzyl chloride. This affords 10.9 g of the desired product as white crystals. mp 74°-76° C. MS(CI): m/z 299(MH+). Calcd for C15H13F3OS: C=60.39, H=4.39, F=19.11, S=10.75 Found C=60.33, H=4.26, F=19.34, S=11.01

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

Procedure: To a solution of 2-(2-Fluoro-phenyl)-1H-pyrrolo[3,2-c]pyridine (50 mg, 0.244 mmole) in DMF (1 ml) was added 10% (w/v) aqueous NaOH (113 μl, 0.28 mmole) followed by a solution of 4-triflouromethoxybenzyl chloride (60 mg, 0.28 mmole) in DMF (0.5 ml). The reaction mixture was stirred at room temperature for 1 hour. The crude reaction mixture was purified by reverse phase HPLC with mass directed collection. Obtained 87 mg (74%) of 2-(2-Fluoro-phenyl)-5-(4-trifluoromethoxy-benzyl)-5H-pyrrolo[3,2-c]pyridinium triflouroacetate. The crude reaction mixture was purified by reverse phase HPLC with mass collection

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

Procedure: To a solution of 2-(2-Fluoro-phenyl)-1H-pyrrolo[3,2-c]pyridine (50 mg, 0.244 mmole) in DMF (1 ml) was added 10% (w/v) aqueous NaOH (113 μl, 0.28 mmole) followed by a solution of 4-triflouromethoxybenzyl chloride (60 mg, 0.28 mmole) in DMF (0.5 ml). The reaction mixture was stirred at room temperature for 1 hour. The crude reaction mixture was purified by reverse phase HPLC with mass directed collection. Obtained 87 mg (74%) of 2-(2-Fluoro-phenyl)-5-(4-trifluoromethoxy-benzyl)-5H-pyrrolo[3,2-c]pyridinium triflouroacetate. The crude reaction mixture was purified by reverse phase HPLC with mass collection

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

Procedure: To a solution of 2-(2-Fluoro-phenyl)-1H-pyrrolo[2,3-c]pyridine (50 mg, 0.244 mmole) in DMF (1 ml) was added 10% (w/v) aqueous NaOH (113 μl, 0.28 mmole) followed by a solution of 4-triflouromethoxybenzyl chloride (60 mg, 0.28 mmole) in DMF (0.5 ml). The reaction mixture was stirred at room temperature for 1 hour. The crude reaction mixture was purified by reverse phase HPLC with mass directed collection. Obtained 9.2 mg (8%) of 2-(2-Fluoro phenyl)-6-(4-trifluoromethoxy-benzyl)-6H-pyrrolo[2,3-c]pyridinium trifluoroacetate after repurification. The crude reaction mixture was purified by reverse phase HPLC with mass collection

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

Procedure: The procedure of Example 87 is repeated using 1.8 g of p-thiocresol and 9.6 g of 4-(trifluoromethoxy)benzyl chloride. This affords 10.9 g of the desired product as white crystals.