Cesium carbonate → 3-[4-(1-carboethoxy-1-(2-phenylethyl)methoxy)-3,5-dipropylphenylmethyl]-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]-pyridine

HRID 1492648Notes

Reaction equation

HRID 1492648 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[CH:29]([CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:30]([O:32][CH2:33][CH3:34])=[O:31].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(Cl)Cl>[C:30]([CH:29]([CH2:35][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=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:32][CH2:33][CH3:34])=[O:31]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 11747666Benzenebutanoic acid, alpha-bromo-, ethyl esterHCID 193856864-(2-Ethyl-5,7-dimethyl-imidazo[4,5-b]pyridin-3-ylmethyl)-2,6-dipropyl-phenol

Product 1

HCID 541604103-[4-(1-carboethoxy-1-(2-phenylethyl)methoxy)-3,5-dipropylphenylmethyl]-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]-pyridineYield 64%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 0.150 g (0.41 mmol) of 5,7-dimethyl-2-ethyl -3-[4-hydroxy-3,5-dipropylphenyl]methyl-3H-imidazol[4,5-β]pyridine (Step G of Example 13) and 0.127 g (0.49 mmol) of ethyl α-bromo-4-phenylbutanoate in 2 mL anhydrous DMF was added 0.290 g (0.82 mmol) cesium carbonate and the reaction mixture was stirred and heated at 60° C. for 4 hours under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, diluted with methylene chloride, filtered, and evaporated in vacuo. The residue was then purified on a silica gel flash chromatography column eluted with 30% EtOAc-hexane. The purified fractions were combined, evaporated and dried in vacuo to afford 0.145 g (64%) of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. customThe residue was then purified on a silica gel flash chromatography column
  5. washeluted with 30% EtOAc-hexane
  6. customevaporated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-dce183b04b094d42baa768256d09d56c
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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