ethyl 3-(4-amino-2-fluorophenyl)propanoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution of 4′-(2-ethoxyethoxy)-2′,3′,5′,6′-tetramethylbiphenyl-3-carbaldehyde (0.300 g, 0.99 mmol) and ethyl 3-(4-amino-2-fluorophenyl)propanoate (0.194 g, 0.99 mmol) in 1,2-dichloroethane (7.0 mL) was added acetic acid (0.158 mL, 2.76 mmol), and the mixture was stirred at room temperature for 3 hr. Sodium triacetoxyborohydride (0.585 g, 2.76 mmol) was added, and the mixture was further stirred for 3 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogencarbonate and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=2/1) to give the title compound (0.400 g, yield 84%) as a colorless oil. the mixture was further stirred for 3 hr washed with saturated aqueous sodium hydrogencarbonate and saturated brine dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=2/1)

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

Procedure: To a solution of 4′-(2-ethoxyethoxy)-2′,3′,5′,6′-tetramethylbiphenyl-3-carbaldehyde (0.300 g, 0.99 mmol) and ethyl 3-(4-amino-2-fluorophenyl)propanoate (0.194 g, 0.99 mmol) in 1,2-dichloroethane (7.0 mL) was added acetic acid (0.158 mL, 2.76 mmol), and the mixture was stirred at room temperature for 3 hr. Sodium triacetoxyborohydride (0.585 g, 2.76 mmol) was added, and the mixture was further stirred for 3 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogencarbonate and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=2/1) to give the title compound (0.400 g, yield 84%) as a colorless oil. the mixture was further stirred for 3 hr washed with saturated aqueous sodium hydrogencarbonate and saturated brine dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=2/1)

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

Procedure: To a solution of 4-[(3,5-diphenyl-1H-pyrazol-1-yl)methyl]-3-isopropoxybenzaldehyde (0.38 g, 0.95 mmol) and ethyl 3-(4-amino-2-fluorophenyl)propanoate (0.20 g, 0.95 mmol) in 1,2-dichloroethane (7.0 mL) was added acetic acid (0.16 mL, 2.86 mmol) and the mixture was stirred at room temperature for 3 hr. Sodium triacetoxyborohydride (0.61 g, 2.86 mmol) was added, and the mixture was further stirred for 3 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-hexane/ethyl acetate=1/1) to give the title compound (0.52 g, yield 92%) as a colorless oil. the mixture was further stirred for 3 hr washed with water and saturated brine dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-hexane/ethyl acetate=1/1)

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

Procedure: To a solution of 4-[(3,5-diphenyl-1H-pyrazol-1-yl)methyl]-3-isopropoxybenzaldehyde (0.38 g, 0.95 mmol) and ethyl 3-(4-amino-2-fluorophenyl)propanoate (0.20 g, 0.95 mmol) in 1,2-dichloroethane (7.0 mL) was added acetic acid (0.16 mL, 2.86 mmol) and the mixture was stirred at room temperature for 3 hr. Sodium triacetoxyborohydride (0.61 g, 2.86 mmol) was added, and the mixture was further stirred for 3 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-hexane/ethyl acetate=1/1) to give the title compound (0.52 g, yield 92%) as a colorless oil. the mixture was further stirred for 3 hr washed with water and saturated brine dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-hexane/ethyl acetate=1/1)

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

Procedure: A mixture of 4′-hydroxy-2′,6′-dimethylbiphenyl-3-carbaldehyde (1.05 g, 4.64 mmol), ethyl 3-(4-amino-2-fluorophenyl)propanoate. (1.00 g, 4.73 mol), acetic acid (0.80 mL, 14 mmol) and 1,2-dichloroethane (20 mL) was stirred at room temperature for 2 hr, and sodium triacetoxyborohydride (3.00 g, 14.2 mmol) was added. The mixture was stirred overnight at room temperature and concentrated. Ethyl acetate was added to the residue, and the mixture was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The mixture was purified by silica gel column chromatography (30% ethyl acetate/hexane) to give the title compound (1.29 g, yield 66%) as a yellow oil. concentrated Ethyl acetate was added to the residue the mixture was washed with water and saturated brine dried over anhydrous magnesium sulfate concentrated under reduced pressure The mixture was purified by silica gel column chromatography (30% ethyl acetate/hexane)