2-chloro-5-methoxybenzaldehyde

Conditions: temp:-40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-bromo-2-chloro-1-iodo-benzene (10.0 g, 31.5 mmol) in THF (120 ml) was added 2 M solution of isopropylmagnesium chloride in THF (17.3 ml, 34.60 mmol) at −65° C. The reaction mixture was stirred at −40° C. for 20 min. After 2-chloro-5-methoxy-benzaldehyde (5.5 g, 32.20 mmol) was added, the reaction mixture was warmed to room temperature and stirred overnight. Then the solution was quenched with saturated aqueous solution of NH4Cl. The aqueous phase was extracted twice with diethyl ether. The combined organic phases were dried over MgSO4 and concentrated in vacuo. The crude material was purified by chromatography (petroleum ether/CH2Cl2 1:1) to provide title compound as a yellowish oil. the reaction mixture was warmed to room temperature stirred overnight Then the solution was quenched with saturated aqueous solution of NH4Cl The aqueous phase was extracted twice with diethyl ether The combined organic phases were dried over MgSO4 concentrated in vacuo The crude material was purified by chromatography (petroleum ether/CH2Cl2 1:1)

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

Procedure: The title compound was prepared from 2-chloro-5-methoxybenzaldehyde, 3-aminopyrazole and ethyl 3-ketohexanoate in the same manner as in Example 25.

Conditions: temp:-40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-bromo-2-chloro-1-iodo-benzene (10.0 g, 31.5 mmol) in THF (120 ml) was added 2 M solution of isopropylmagnesium chloride in THF (17.3 ml, 34.60 mmol) at −65° C. The reaction mixture was stirred at −40° C. for 20 min. After 2-chloro-5-methoxy-benzaldehyde (5.5 g, 32.20 mmol) was added, the reaction mixture was warmed to room temperature and stirred overnight. Then the solution was quenched with saturated aqueous solution of NH4Cl. The aqueous phase was extracted twice with diethyl ether. The combined organic phases were dried over MgSO4 and concentrated in vacuo. The crude material was purified by chromatography (petroleum ether/CH2Cl2 1:1) to provide title compound as a yellowish oil. the reaction mixture was warmed to room temperature stirred overnight Then the solution was quenched with saturated aqueous solution of NH4Cl The aqueous phase was extracted twice with diethyl ether The combined organic phases were dried over MgSO4 concentrated in vacuo The crude material was purified by chromatography (petroleum ether/CH2Cl2 1:1)

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

Procedure: The title compound was prepared from 2-chloro-5-methoxybenzaldehyde, 3-aminopyrazole and ethyl 3-ketohexanoate in the same manner as in Example 25.