(3-ethoxyphenyl)methanamine

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:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (1-Butyl-2-iodo-4-phenyl-3H-imidazol-5-yl)-methanol (1.96 g), prepared by the method given in Example 2, step 2, is dissolved in 20 mL CH2Cl2. The solution is cooled to 0° C. and 3 equivalents of SOCl2 are added. The resulting solution is stirred at room temperature for 2 hours and then evaporated to dryness. The residue is dissolved in 5 mL of DMF and added to an ice cooled solution of 2 equivalents of 3-ethoxybenzylamine and 2 equivalents K2CO3 in 10 mL DMF. The mixture is stirred overnight at room temperature. The reaction is quenched with 20 mL water, extracted with EtOAc (3×30 mL), washed with water and brine, and dried over Na2SO4. Concentration and purification via silica gel chromatography provides (1-Butyl-2-iodo-4-phenyl-3H-imidazol-5-ylmethyl)-(3-ethoxy-benzyl)-amine. evaporated to dryness The residue is dissolved in 5 mL of DMF The mixture is stirred overnight at room temperature The reaction is quenched with 20 mL water extracted with EtOAc (3×30 mL) washed with water and brine dried over Na2SO4 Concentration and purification via silica gel chromatography

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

Procedure: Prepared according to the procedure described for example 50 from 5-[(3,5-dichloro-4-pyridyl)sulfanyl]-4-nitro-thiophene-2-carbonyl chloride (120 mg, 0.33 mmol) and 3-ethoxybenzylamine (58.3 mg, 0.39 mmol). The title compound was obtained as a solid (71 mg, 45% yield). 1H NMR (400 MHz, d6-DMSO) δ: 9.36 (1H, m), 8.99 (2H, s), 8.48 (1H, s), 7.22 (1H, m), 6.81 (3H, m), 4.36 (2H, m), 3.99 (2H, q), 1.30 (3H, t). MS m/z: 482.13, 484.10 [M+H]+. Prepared