N-[(4-bromophenyl)methyl]propan-2-amine

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Following the procedure described in Example 1, process variant (a), 23 g of N-(4-bromobenzyl)-N-isopropylamine were reacted with 14 g of phenyl isothiocyanate. 32 g of N-(4-bromobenzyl)-N-isopropyl-N'-phenylthiourea were obtained. Yield: 88%. Melting point: 133.5°-134.5° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Following the procedure described in Example 1, process variant (a), 23 g of N-(4-bromobenzyl)-N-isopropylamine were reacted with 14 g of phenyl isothiocyanate. 32 g of N-(4-bromobenzyl)-N-isopropyl-N'-phenylthiourea were obtained. Yield: 88%. Melting point: 133.5°-134.5° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Following the procedure described in Example 1, process variant (a), 23 g of N-(4-bromobenzyl)-N-isopropylamine were reacted with 14 g of phenyl isothiocyanate. 32 g of N-(4-bromobenzyl)-N-isopropyl-N'-phenylthiourea were obtained. Yield: 88%. Melting point: 133.5°-134.5° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 1-bromo-4-(bromomethyl)benzene (2.0 g, 8.0 mmol), isopropylamine (950 mg, 16 mmol) and potassium carbonate (2.2 g, 16 mmol) in acetonitrile (40 mL) was stirred at room temperature for 18 h. The reaction mixture was quenched with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography (silica, 0-100% methylene chloride/methanol) to afford the desired product (1.4 g, 78%) as a brown solid: ESI MS m/z 228 [C10H14BrN+H]+. The reaction mixture was quenched with water extracted with ethyl acetate The combined organic layers were washed with brine dried over anhydrous sodium sulfate filtered concentrated The residue was purified by column chromatography (silica, 0-100% methylene chloride/methanol)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Following General Procedure E, N-(4-bromobenzyl)propan-2-amine (200 mg, 0.88 mmol) was reacted with bis(pinacolato)diboron (240 mg, 0.96 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (270 mg, 0.88 mmol) to afford the desired product (190 mg, 57%) as a light brown solid: 1H NMR (500 MHz, CD3CD2OD) δ 7.68-7.63 (m, 2H), 7.56-7.49 (m, 2H), 7.41-7.34 (m, 3H), 6.04 (dd, J=5.4, 2.4 Hz, 1H), 4.33 (s, 2H), 3.72-3.67 (m, 3H), 3.56-3.50 (m, 1H), 1.45 (dd, J=6.6, 2.2 Hz, 6H). to afford the crude boronic ester which

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Following the procedure described in Example 1, process variant (a), 23 g of N-(4-bromobenzyl)-N-isopropylamine were reacted with 14 g of phenyl isothiocyanate. 32 g of N-(4-bromobenzyl)-N-isopropyl-N'-phenylthiourea were obtained. Yield: 88%. Melting point: 133.5°-134.5° C.