2-(4-Fluorophenyl)-1-(6-methylpyridin-2-yl)ethanone → HCID 86592626, compound

HRID 8231Notes

Reaction equation

HRID 8231 reaction equation
[NH2:1][N:2]1[C@H:6]([CH2:7][O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:4][C:3]1=[O:16].[F:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[N:28]=2)=O)=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[CH2:9]([O:8][CH2:7][C@H:6]1[N:2]([N:1]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[N:28]=2)[CH2:24][C:21]2[CH:20]=[CH:19][C:18]([F:17])=[CH:23][CH:22]=2)[C:3](=[O:16])[CH2:4][CH2:5]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 219925362-(4-Fluorophenyl)-1-(6-methylpyridin-2-yl)ethanoneHCID 69364858HCID 69364858, compound

Product 1

HCID 86592626HCID 86592626, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of (S)-1-amino-5-benzyloxymethyl-pyrrolidin-2-one (0.5 g, 2.27 mmol) and 2-(4-fluoro-phenyl)-1-(6-methyl-pyridin-2-yl)-ethanone (0.52 g, 2.27 mmol) in toluene (2.5 mL) in a round bottom flask equipped with a Dean-Stark apparatus is refluxed for 1 h. The mixture is concentrated in vacuo and the residue chromatographed on SiO2 (40% ethyl acetate/hexanes) to yield the title compound, 500 mg (52%), as a pale yellow oil.

Workup

  1. customequipped with a Dean-Stark apparatus
  2. temperatureis refluxed for 1 h
  3. concentrationThe mixture is concentrated in vacuo
  4. customthe residue chromatographed on SiO2 (40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-107ff0fc209646f1a567aa9737b3f702
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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