Propargyl bromide → 5-(4-Chloro-phenyl)-2-prop-2-ynyloxy-pyridine

HRID 1916727Notes

Reaction equation

HRID 1916727 reaction equation
Br[CH2:2][C:3]#[CH:4].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]([OH:18])=[N:16][CH:17]=2)=[CH:8][CH:7]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:4][C:3]#[CH:2])=[N:16][CH:17]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 178515864HCID 178515864, compound

Product 1

HCID 859696065-(4-Chloro-phenyl)-2-prop-2-ynyloxy-pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 mL (80% in toluene, 18.5 mmol) 3-bromo-propyne are added to a suspension of 3.8 g (18.5 mmol) 5-(4-chloro-phenyl)-pyridin-2-ol and 5.1 g (37 mmol) K2CO3 in 50 mL DMF and the reaction mixture is stirred for 64 h at RT. The mixture is evaporated down i. vac., the residue is combined with 80 mL water, extracted with 150 mL EtOAc and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, cyc/EtOAc 2:1).

Workup

  1. customThe mixture is evaporated down i
  2. extractionextracted with 150 mL EtOAc
  3. dry with materialthe organic phase is dried over Na2SO4
  4. customis purified by chromatography (silica gel, cyc/EtOAc 2:1)

Sources & evidence

ORD record
ord-2fbb8cdabd9e41b390e925e98188f3c7
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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