4'-(2-Ethoxyethoxy)-2',6'-dimethylbiphenyl-3-carbaldehyde → Ethyl 3-[4-({[4'-(2-ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methyl}amino)phenyl]-2-fluoropropanoate

HRID 508044Notes

Reaction equation

HRID 508044 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([F:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[CH2:16]([O:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([CH:35]=O)[CH:30]=2)=[C:24]([CH3:37])[CH:23]=1)[CH3:17]>C1(C)C=CC=CC=1>[CH2:16]([O:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][NH:1][C:2]3[CH:3]=[CH:4][C:5]([CH2:8][CH:9]([F:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=3)[CH:30]=2)=[C:24]([CH3:37])[CH:23]=1)[CH3:17]

Participants

4

Reactant 2

HCID 231117224'-(2-Ethoxyethoxy)-2',6'-dimethylbiphenyl-3-carbaldehydeHCID 23157378Ethyl 3-(4-aminophenyl)-2-fluoropropanoate

Product 1

HCID 23157227Ethyl 3-[4-({[4'-(2-ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methyl}amino)phenyl]-2-fluoropropanoateYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of ethyl 3-(4-aminophenyl)-2-fluoropropanoate (400 mg, 1.89 mmol) and 4′-(2-ethoxyethoxy)-2′,6′-dimethylbiphenyl-3-carbaldehyde (434 mg, 1.45 mmol) in toluene (25 mL) were added molecular sieves (0.4 nm, beads, 1.6 g), and the mixture was stirred at room temperature for 16 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in tetrahydrofuran (20 mL) and ethanol (20 mL), 10% palladium-carbon (50% water-containing product, 0.40 g) was added, and the mixture was stirred under a hydrogen atmosphere (balloon pressure) at room temperature for 3 hr. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5%-40% hexane/ethyl acetate) to give the title compound (320 mg, yield 45%) as a colorless oil.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe obtained residue was dissolved in tetrahydrofuran (20 mL)
  4. additionethanol (20 mL), 10% palladium-carbon (50% water-containing product, 0.40 g) was added
  5. stirringthe mixture was stirred under a hydrogen atmosphere (balloon pressure) at room temperature for 3 hr
  6. filtrationThe catalyst was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (5%-40% hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5534b5a4ec714afaa68670275cf4ba3f
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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