Potassium Carbonate → 3-[4-(1-carbomethoxy-1-phenylmethoxy)-3,5-dipropylphenylmethyl]-5,7-dimethyl-2-ethyl-3H-imidazo-[4,5-b]pyridine

HRID 1492608Notes

Reaction equation

HRID 1492608 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:13][C:14]3[CH:19]=[C:18]([CH2:20][CH2:21][CH3:22])[C:17]([OH:23])=[C:16]([CH2:24][CH2:25][CH3:26])[CH:15]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:27])[CH:3]=1.Br[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][C:36]([O:38][CH3:39])=[O:37].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:36]([CH:35]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:29]=1)[O:23][C:17]1[C:16]([CH2:24][CH2:25][CH3:26])=[CH:15][C:14]([CH2:13][N:8]2[C:6]3=[N:7][C:2]([CH3:1])=[CH:3][C:4]([CH3:27])=[C:5]3[N:10]=[C:9]2[CH2:11][CH3:12])=[CH:19][C:18]=1[CH2:20][CH2:21][CH3:22])([O:38][CH3:39])=[O:37]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 8063364Methyl 2-(2-bromophenyl)acetateHCID 193856864-(2-Ethyl-5,7-dimethyl-imidazo[4,5-b]pyridin-3-ylmethyl)-2,6-dipropyl-phenol

Product 1

HCID 193856093-[4-(1-carbomethoxy-1-phenylmethoxy)-3,5-dipropylphenylmethyl]-5,7-dimethyl-2-ethyl-3H-imidazo-[4,5-b]pyridineYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (4.72 mmol) of the product of Step G and (5.19 mmol) of methyl 2-bromophenylacetate in 10 mL of acetone was added (9.44 mmol) of K2CO3 and the mixture was stirred and refluxed for 14 hours. The mixture was cooled, filtered and evaporated in vacuo and the residue was purified on a silica gel flash chromatography column to afford a 96% yield of the title compound.

Workup

  1. temperaturerefluxed for 14 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customthe residue was purified on a silica gel flash chromatography column

Sources & evidence

ORD record
ord-092f422b193a4ac6be10cff2f19d5d67
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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