Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | Ethyl 3-(4-amino-2-fluorophenyl)propanoate | HCID 23157234 | — |
| Reactant | HCID 23157293 | HCID 23157293 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 23157486 | HCID 23157486 | 92.5% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07786165B2 |
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| Source dataset | uspto-grants-2010_08 |
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| ORD ID | ord-28c578dd04a047bfb2747026da1faa21 |
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| Source note | uspto-grants-2010_08 |
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