Pyridine → Ethyl 3-{4-[(4'-{2-[acetyl(ethyl)amino]ethoxy}-2',6'-dimethylbiphenyl-3-yl)methoxy]-2-fluorophenyl}propanoate

HRID 273416Notes

Reaction equation

HRID 273416 reaction equation
[CH2:1]([NH:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:24]([F:35])[CH:23]=3)[CH:15]=2)=[C:9]([CH3:36])[CH:8]=1)[CH3:2].C(OC(=O)C)(=[O:39])C.N1[CH:49]=[CH:48]C=CC=1>CN(C)C1C=CN=CC=1>[C:1]([N:3]([CH2:48][CH3:49])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:24]([F:35])[CH:23]=3)[CH:15]=2)=[C:9]([CH3:36])[CH:8]=1)(=[O:39])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 58903118Ethyl 3-[4-({4'-[2-(ethylamino)ethoxy]-2',6'-dimethylbiphenyl-3-yl}methoxy)-2-fluorophenyl]propanoate

Product 1

HCID 58903168Ethyl 3-{4-[(4'-{2-[acetyl(ethyl)amino]ethoxy}-2',6'-dimethylbiphenyl-3-yl)methoxy]-2-fluorophenyl}propanoateYield 85%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A mixture of ethyl 3-[4-({4′-[2-(ethylamino)ethoxy]-2′,6′-dimethylbiphenyl-3-yl}methoxy)-2-fluorophenyl]propanoate (0.27 g, 0.55 mmol), 4-dimethylaminopyridine (7 mg, 55 μmol), acetic anhydride (0.10 mL, 1.09 mmol) and pyridine (5.4 mL) was stirred at room temperature for 62 hrs. The reaction mixture was concentrated and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-ethyl acetate) to give the title compound (0.25 g, yield 85%) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-ethyl acetate)

Sources & evidence

ORD record
ord-ddf954f55169456eba2260a5b2e61ac6
Source dataset
uspto-grants-2008_11
Patent number
US07456218B2

Reaction notes

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