Acetic Acid → HCID 23157486, compound

HRID 508083Notes

Reaction equation

HRID 508083 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:9]([CH2:18][C:19]3[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][C:20]=3[O:27][CH:28]([CH3:30])[CH3:29])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[C:34]([F:45])[CH:33]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(OCC)(=O)C>[C:1]1([C:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:9]([CH2:18][C:19]3[CH:26]=[CH:25][C:22]([CH2:23][NH:31][C:32]4[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[C:34]([F:45])[CH:33]=4)=[CH:21][C:20]=3[O:27][CH:28]([CH3:30])[CH3:29])[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 23157234Ethyl 3-(4-amino-2-fluorophenyl)propanoateHCID 23157293HCID 23157293, compound

Product 1

HCID 23157486HCID 23157486, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

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.

Workup

  1. stirringthe mixture was further stirred for 3 hr
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-28c578dd04a047bfb2747026da1faa21
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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