HCID 59434119, compound → HCID 23157533, compound

HRID 508001Notes

Reaction equation

C([N:8](CC1C=CC=CC=1)[C:9]1[CH:14]=[C:13]([F:15])[C:12](/[CH:16]=[CH:17]/[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:11]([F:23])[CH:10]=1)C1C=CC=CC=1>C(O)(=O)C.[C].[Pd]>[NH2:8][C:9]1[CH:10]=[C:11]([F:23])[C:12]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:13]([F:15])[CH:14]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl(2E)-3-[4-(dibenzylamino)-2,6-difluorophenyl]acrylate (5.00 g, 12.3 mmol) in acetic acid (100 mL) was added 10% palladium-carbon (50% water-containing product, 0.50 g), and the mixture was stirred under a hydrogen atmosphere at 50° C. for 16 hr. The catalyst was filtered off, and the obtained filtrate was concentrated. The residue was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5-hexane/ethyl acetate=50/50) to give the title compound (2.63 g, yield 93%) as a yellow oil.

Workup

filtrationThe catalyst was filtered off
concentrationthe obtained filtrate was concentrated
additionThe residue was diluted with ethyl acetate
washwashed with saturated aqueous sodium hydrogencarbonate and saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5-hexane/ethyl acetate=50/50)

Sources & evidence

ORD record: ord-0ecf6621d2fe405cb44e16116a131cb0
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786165B2

Reaction notes

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