Sodium Chloride → 1-[5-(2-Ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)-thiophen-2-yl]cyclopent-3ene carboxylic acid ethyl ester

HRID 481390Notes

Reaction equation

HRID 481390 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[NH:6][C:7]2[C:8]([N:15]=1)=[N:9][C:10]([CH3:14])=[CH:11][C:12]=2[CH3:13])[CH3:4].[CH2:16]([O:18][C:19]([C:21]1([C:26]2[S:27][C:28]([CH2:31]Cl)=[CH:29][CH:30]=2)[CH2:25][CH:24]=[CH:23][CH2:22]1)=[O:20])[CH3:17].[Na+].[Cl-]>CN(C=O)C>[CH2:16]([O:18][C:19]([C:21]1([C:26]2[S:27][C:28]([CH2:31][N:15]3[C:8]4=[N:9][C:10]([CH3:14])=[CH:11][C:12]([CH3:13])=[C:7]4[N:6]=[C:5]3[CH2:3][CH3:4])=[CH:29][CH:30]=2)[CH2:25][CH:24]=[CH:23][CH2:22]1)=[O:20])[CH3:17]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 98153742,6-Dimethyl-8-ethyl-1-deazapurineHCID 545331371-(5-Chloromethylthiophen-2-yl)-cyclopent-3-ene carboxylic acid ethyl ester2×

Product 1

HCID 684276321-[5-(2-Ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)-thiophen-2-yl]cyclopent-3ene carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of petroleum ether washed NaH (1.1 equiv.) in DMF was added 2-ethyl-5,7-dimethylimidazo[4,5-b]pyridine (7) (1.1 equiv.). The reaction mixture was stirred for 15 minutes at ambient temperature and then the product of Step 4, above (5) (1 equiv.), dissolved in DMF, was cannulated into the mixture of the anion in DMF. The reaction mixture was stirred at ambient temperature for 17 hours and was then poured into saturated NaCl solution and extracted 2 times with EtOAc. The combined extracts were dried over MgSO4, filtered and concentrated to dryness. The crude material was chromatographed on silica gel with a gradient elution from 50% EtOAc in hexanes to 60% EtOAc in hexanes to yield the title compound (6).

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 17 hours
  2. extractionextracted 2 times with EtOAc
  3. dry with materialThe combined extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude material was chromatographed on silica gel with a gradient elution from 50% EtOAc in hexanes to 60% EtOAc in hexanes

Sources & evidence

ORD record
ord-69a29ed454984e2195e21b9f52181d1f
Source dataset
uspto-grants-1998_08
Patent number
US05789415

Reaction notes

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