(3-chloro-2-fluorophenyl)hydrazine

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

Procedure: The title compound, EI-MS: m/e=258.1 (M+), was prepared in accordance with the general method of example 25b) from (3-Chloro-2-fluoro-phenyl)-hydrazine and ethyl pyruvate.

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

Procedure: The title compound, EI-MS: m/e=258.1 (M+), was prepared in accordance with the general method of example 25b) from (3-Chloro-2-fluoro-phenyl)-hydrazine and ethyl pyruvate.

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

Procedure: The title compound, EI-MS: m/e=258.1 (M+), was prepared in accordance with the general method of example 25b) from (3-Chloro-2-fluoro-phenyl)-hydrazine and ethyl pyruvate.

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

Procedure: The title compound, EI-MS: m/e=258.1 (M+), was prepared in accordance with the general method of example 25b) from (3-Chloro-2-fluoro-phenyl)-hydrazine and ethyl pyruvate.

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-butyryl-2-hydroxy-benzoic acid methyl ester (60 mg, 0.27 mmol), (3-chloro-2-fluoro-phenyl)-hydrazine (Apollo Scientific, Ltd., 54 mg, 0.27 mmol), and zinc chloride (110 mg, 0.8 mmol) in acetic acid (2 mL) is purged with nitrogen for 5 minutes and then heated in a sealed tube at 120° C. for 2 hours. The mixture is cooled to room temperature and diluted with ethyl acetate. The resulting mixture is sequentially washed with saturated aqueous Na2CO3 and saturated aqueous NaCl, and finally dried over sodium sulfate. After concentration, the crude product is purified via silica gel flash column chromatography (10% ethyl acetate in hexanes) to afford 4-(6-chloro-3-ethyl-7-fluoro-1H-indol-2-yl)-2-hydroxy-benzoic acid methyl ester as a light yellow solid: ESMS m/z 348.1 (M+H+). is purged with nitrogen for 5 minutes The mixture is cooled to room temperature diluted with ethyl acetate The resulting mixture is sequentially washed with saturated aqueous Na2CO3 and saturated aqueous NaCl finally dried over sodium sulfate After concentration the crude product is purified via silica gel flash column chromatography (10% ethyl acetate in hexanes)

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

Procedure: The title compound, EI-MS: m/e=258.1 (M+), was prepared in accordance with the general method of example 25b) from (3-Chloro-2-fluoro-phenyl)-hydrazine and ethyl pyruvate.

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

Procedure: The product was obtained starting from 3-((E)-3-Dimethylamino-acryloyl)-1-(3-trifluoromethansulfonyl-phenyl)-1H-pyridazin-4-one (A-33) and 3-chloro-2-fluoro-phenylhydrazine according to the method described for example 1. MS: M=499.0 (M+H)+ The product was obtained

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

Procedure: The product was obtained starting from 3-((E)-3-Dimethylamino-acryloyl)-1-(4-trifluoromethansulfonyl-phenyl)-1H-pyridazin-4-one (A-27) and 3-chloro-2-fluoro-phenylhydrazine according to the method described for example 1. MS: M=499.0 (M+H)+ The product was obtained

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

Procedure: The title compound, EI-MS: m/e=258.1 (M+), was prepared in accordance with the general method of example 32d) from (3-Chloro-2-fluoro-phenyl)-hydrazine and ethyl pyruvate.

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

Procedure: The title compound, EI-MS: m/e=258.1 (M+), was prepared in accordance with the general method of example 25b) from (3-Chloro-2-fluoro-phenyl)-hydrazine and ethyl pyruvate.