Potassium Carbonate → 2-[1-[3-(3-(3-Pyridyl)prop-2-yn-1-yloxy)phenyl]-1-methoxypropyl]thiazole

HRID 1974506Notes

Reaction equation

HRID 1974506 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)([O:11][CH3:12])[CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[C:32][CH2:33]Br)[CH:26]=1>CC(C)=O>[N:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[C:32][CH2:33][O:1][C:2]2[CH:3]=[C:4]([C:8]([C:13]3[S:14][CH:15]=[CH:16][N:17]=3)([O:11][CH3:12])[CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=2)[CH:26]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 156373793-[1-Methoxy-1-(1,3-thiazol-2-yl)propyl]phenolHCID 167329213-(3-Bromoprop-1-ynyl)pyridine hydrobromide

Product 1

HCID 191016422-[1-[3-(3-(3-Pyridyl)prop-2-yn-1-yloxy)phenyl]-1-methoxypropyl]thiazoleYield 59.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-[1-(3-hydroxyphenyl)-1-methoxypropyl]thiazole (0.25 g), potassium carbonate (0.28 g), 3-(3-pyridyl)prop-2-yn-1-yl bromide hydrobromide (0.28 g) and acetone (5 ml) was stirred and heated to reflux for 17 hours. The mixture was cooled to ambient temperature, filtered and the filtrate was evaporated. The residue was purified by column chromatography eluting with hexane/ethyl acetate (1:1 v/v) to give 2-[1-[3-(3-(3-pyridyl)prop-2-yn-1-yloxy)phenyl]-1-methoxypropyl]thiazole as an oil (0.217 g, 59%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 17 hours
  3. filtrationfiltered
  4. customthe filtrate was evaporated
  5. customThe residue was purified by column chromatography
  6. washeluting with hexane/ethyl acetate (1:1 v/v)

Sources & evidence

ORD record
ord-37ae93597e0b440f89003812c7da6dbf
Source dataset
uspto-grants-1994_02
Patent number
US05283245

Reaction notes

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