2-Bromo-1-(5-bromo-2-methoxyphenyl)ethanone

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

Procedure: The title compound was prepared in analogy to example 1 step e) from 232 mg (0.75 mmol) 2-bromo-1-(5-bromo-2-methoxyphenyl)ethanone and 170 mg (0.68 mmol) (4-imidazol-1-yl-3-methoxy-phenyl)-thiourea yielding 130 mg (41%) [4-(5-bromo-2-methoxy-phenyl)-thiazol-2-yl]-(4-imidazol-1-yl-3-methoxy-phenyl)-amine as a light yellow solid. MS ISP (m/e): 457.1/459.3 (100/90) (M+H)+.

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

Procedure: The title compound was prepared in analogy to example 1 step e) from 232 mg (0.75 mmol) 2-bromo-1-(5-bromo-2-methoxyphenyl)ethanone and 170 mg (0.68 mmol) (4-imidazol-1-yl-3-methoxy-phenyl)-thiourea yielding 130 mg (41%) [4-(5-bromo-2-methoxy-phenyl)-thiazol-2-yl]-(4-imidazol-1-yl-3-methoxy-phenyl)-amine as a light yellow solid. MS ISP (m/e): 457.1/459.3 (100/90) (M+H)+.

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

Procedure: The title compound was prepared in analogy to example 1 step e) from 102 mg (0.33 mmol) 2-bromo-1-(5-bromo-2-methoxyphenyl)ethanone and 79 mg (0.3 mmol) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea. The crude reaction was diluted with diethyl ether and stirred for 15 minutes at room temperature. The product was filtered off and dried to yield 147 mg (99%) [4-(5-bromo-2-methoxy-phenyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine as a white solid. MS ISP (m/e): 472.8/470.9 (100/93) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.74 (s, 1H), 9.30 (s, 1H), 8.34 (dd, 1H), 7.70 (s, 1H), 7.60 (s, 1H), 7.51 (d, 1H), 7.47 (d, 1H), 7.13 (d, 1H), 7.05 (d, 1H), 4.00 (s, 3H), 3.95 (s, 3H), 2.35 (s, 3H). The crude reaction The product was filtered off dried

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 2-bromo-1-(5-bromo-2-methoxyphenyl)ethanone (500 mg, 1.6 mmol) in EtOH (5 mL), pyridin-2-amine (153 mg, 1.6 mmol) was added. The mixture was stirred at 80° C. for 12 hours, and then cooled to 25° C. After filtrated, the solid was dried in vacuo to provide 2-(5-bromo-2-methoxyphenyl)imidazo[1,2-a]pyridine (30 mg, yield: 5%). 1H-NMR(CDCl3, 400 MHz) δ 8.54 (s, 1H), 8.18 (s, 1H), 8.12˜8.13 (m, 1H), 7.62˜7.64 (m, 1H), 7.37˜7.40 (m, 1H), 7.16˜7.21 (m, 1H), 6.86˜6.88 (m, 1H), 6.76˜6.79 (m, 1H), 3.98 (s, 3H). MS (M+H)+: 303/305. was added cooled to 25° C After filtrated the solid was dried in vacuo

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

Procedure: The title compound was prepared in analogy to example 1 step e) from 232 mg (0.75 mmol) 2-bromo-1-(5-bromo-2-methoxyphenyl)ethanone and 170 mg (0.68 mmol) (4-imidazol-1-yl-3-methoxy-phenyl)-thiourea yielding 130 mg (41%) [4-(5-bromo-2-methoxy-phenyl)-thiazol-2-yl]-(4-imidazol-1-yl-3-methoxy-phenyl)-amine as a light yellow solid. MS ISP (m/e): 457.1/459.3 (100/90) (M+H)+.

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

Procedure: The title compound was prepared in analogy to example 1 step e) from 102 mg (0.33 mmol) 2-bromo-1-(5-bromo-2-methoxyphenyl)ethanone and 79 mg (0.3 mmol) [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea. The crude reaction was diluted with diethyl ether and stirred for 15 minutes at room temperature. The product was filtered off and dried to yield 147 mg (99%) [4-(5-bromo-2-methoxy-phenyl)-thiazol-2-yl]-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine as a white solid. MS ISP (m/e): 472.8/470.9 (100/93) (M+H)+. 1H NMR (DMSO-D6, 250 MHz): δ (ppm)=10.74 (s, 1H), 9.30 (s, 1H), 8.34 (dd, 1H), 7.70 (s, 1H), 7.60 (s, 1H), 7.51 (d, 1H), 7.47 (d, 1H), 7.13 (d, 1H), 7.05 (d, 1H), 4.00 (s, 3H), 3.95 (s, 3H), 2.35 (s, 3H). The crude reaction The product was filtered off dried