Benzenebutanoic acid, 4-broMo-.alpha.,.gaMMa.-dioxo-, ethyl este

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The title compound was prepared in the same manner as described for intermediate 61 using ethyl 4-(4-bromophenyl)-2,4-dioxobutanoate (956 mg, 3.20 mmol), benzene (10 mL), 1-(1-methylethyl)-1H-pyrazol-5-amine (400 mg, 3.20 mmol), and acetic acid (4 mL). The crude product was purified using column chromatography (Silica gel, eluent: 0 to 100% EtOAc/hexanes) to give 1.1 g (89%) of product. LCMS E-S (M+H)=388.1. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.49-1.57 (t, J=67.2 Hz, 3H), 1.63-1.74 (d, J=6.8 Hz 6H), 4.56 (q, J=7.2 Hz, 2H), 5.46 (spt, J=6.7 Hz, 1H), 7.65-7.71 (m, 2H), 8.04-8.15 (m, 2H), 8.21 (s, 1H), 8.42 (s, 1H). The crude product was purified

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The title compound was prepared in the same manner as for intermediate 66 using sodium metal (0.404 g, 17.58 mmol), 1-(4-bromophenyl)ethanone (3.5 g, 17.58 mmol), and diethyl ethanedioate (2.384 mL, 17.58 mmol). The product was collected as 5.1 g (97%). LCMS E-S (M+H)=299.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.22-1.37 (m, 3H), 4.25 (d, J=6.57 Hz, 2H), 7.72 (m, 2H), 7.92 (m, 2H). The product was collected as 5.1 g (97%)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The title compound was prepared in the same manner as described for intermediate 61 using ethyl 4-(4-bromophenyl)-2,4-dioxobutanoate (956 mg, 3.20 mmol), benzene (10 mL), 1-(1-methylethyl)-1H-pyrazol-5-amine (400 mg, 3.20 mmol), and acetic acid (4 mL). The crude product was purified using column chromatography (Silica gel, eluent: 0 to 100% EtOAc/hexanes) to give 1.1 g (89%) of product. LCMS E-S (M+H)=388.1. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.49-1.57 (t, J=67.2 Hz, 3 H), 1.63-1.74 (d, J=6.8 Hz 6 H), 4.56 (q, J=7.2 Hz, 2 H), 5.46 (spt, J=6.7 Hz, 1 H), 7.65-7.71 (m, 2 H), 8.04-8.15 (m, 2 H), 8.21 (s, 1 H), 8.42 (s, 1 H). The crude product was purified

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The title compound was prepared in the same manner as for intermediate 66 using sodium metal (0.404 g, 17.58 mmol), 1-(4-bromophenyl)ethanone (3.5 g, 17.58 mmol), and diethyl ethanedioate (2.384 mL, 17.58 mmol). The product was collected as 5.1 g (97%). LCMS E-S (M+H)=299.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.22-1.37 (m, 3 H), 4.25 (d, J=6.57 Hz, 2 H), 7.72 (m, 2 H), 7.92 (m, 2 H). The product was collected as 5.1 g (97%)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The title compound was prepared in the same manner as described for intermediate 61 using ethyl 4-(4-bromophenyl)-2,4-dioxobutanoate (956 mg, 3.20 mmol), benzene (10 mL), 1-(1-methylethyl)-1H-pyrazol-5-amine (400 mg, 3.20 mmol), and acetic acid (4 mL). The crude product was purified using column chromatography (Silica gel, eluent: 0 to 100% EtOAc/hexanes) to give 1.1 g (89%) of product. LCMS E-S (M+H)=388.1. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.49-1.57 (t, J=67.2 Hz, 3H), 1.63-1.74 (d, J=6.8 Hz 6H), 4.56 (q, J=7.2 Hz, 2H), 5.46 (spt, J=6.7 Hz, 1H), 7.65-7.71 (m, 2H), 8.04-8.15 (m, 2H), 8.21 (s, 1H), 8.42 (s, 1H). The crude product was purified

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The title compound was prepared in the same manner as for intermediate 66 using sodium metal (0.404 g, 17.58 mmol), 1-(4-bromophenyl)ethanone (3.5 g, 17.58 mmol), and diethyl ethanedioate (2.384 mL, 17.58 mmol). The product was collected as 5.1 g (97%). LCMS E-S (M+H)=299.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.22-1.37 (m, 3H), 4.25 (d, J=6.57 Hz, 2H), 7.72 (m, 2H), 7.92 (m, 2H). The product was collected as 5.1 g (97%)