Water → (S)-N-(1-{4-[3-(2-Fluoro-pyridin-4-yloxy)-azetidin-1-yl]-phenyl}-ethyl)-acetamide

HRID 40510

Reaction equation

HRID 40510 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]2[CH:11]=[CH:10][C:9]([C@@H:12]([NH:14][C:15](=[O:17])[CH3:16])[CH3:13])=[CH:8][CH:7]=2)[CH2:3]1.[F:18][C:19]1[CH:24]=[C:23](F)[CH:22]=[CH:21][N:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[F:18][C:19]1[CH:24]=[C:23]([O:1][CH:2]2[CH2:3][N:4]([C:6]3[CH:7]=[CH:8][C:9]([C@@H:12]([NH:14][C:15](=[O:17])[CH3:16])[CH3:13])=[CH:10][CH:11]=3)[CH2:5]2)[CH:22]=[CH:21][N:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27628382,4-DifluoropyridineHCID 86689005(S)-N-{1-[4-(3-Hydroxy-azetidin-1-yl)-phenyl]ethyl}-acetamide

Product 1

HCID 86689013(S)-N-(1-{4-[3-(2-Fluoro-pyridin-4-yloxy)-azetidin-1-yl]-phenyl}-ethyl)-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1.0 g (4.3 mmol) (S)—N-{1-[4-(3-Hydroxy-azetidin-1-yl)-phenyl]-ethyl}-acetamide (V.1), 0.6 g (5.2 mmol) 2,4-difluoropyridine and 2.0 g (6.2 mmol) cesium carbonate are combined in 40 mL DMF and the mixture is stirred for 12 h at 80° C. Water is added and the mixture is extracted twice with ethylacetate. After concentration in vacuo the residue is purified by chromatography (silica; ethylacetate) to yield the desired product.

Workup

  1. extractionthe mixture is extracted twice with ethylacetate
  2. concentrationAfter concentration in vacuo the residue
  3. customis purified by chromatography (silica; ethylacetate)

Sources & evidence

ORD record
ord-85a0c2d0eaa043fabddad6d68fafa6c6
Source dataset
uspto-grants-2013_09
Patent number
US08530461B2

Linked notes

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