Ethyl Acetate → HCID 19385639, compound

HRID 1492633Notes

Reaction equation

HRID 1492633 reaction equation
[CH2:1]([C:3]1[N:16]=[C:6]2[NH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].[H-].[Na+].Br[CH2:20][C:21]1[CH:41]=[CH:40][C:24]([O:25][CH:26]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[C:23]([CH2:42][CH2:43][CH3:44])[CH:22]=1.CCOC(C)=O>CN(C=O)C>[C:27]([CH:26]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[O:25][C:24]1[CH:40]=[CH:41][C:21]([CH2:20][N:16]2[C:6]3=[N:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][C:10]([CH3:11])=[C:5]3[N:4]=[C:3]2[CH2:1][CH3:2])=[CH:22][C:23]=1[CH2:42][CH2:43][CH3:44])([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 19385655HCID 19385655, compoundHCID 178437553HCID 178437553, compound2×

Product 1

HCID 19385639HCID 19385639, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 25 mL round bottom flask were placed 41.8 mg (0.19 mmol) of methyl 2-ethyl-7-methylimidazo[4,5-b]pyridine-5-carboxylate (the product of Step G of this Example) and a 60% oil dispersion of NaH (5 mg, 0.21 mmol). The flask was evacuated and filled with nitrogen. Dry DMF (2 mL) was added to the mixture dropwise at 0° C. The solution was stirred at rt for 5 minutes. To the solution was added 80 mg (0.19 mmol) of tert-butyl 2-(4-bromomethyl-2-propyl- phenoxy)-2-phenylacetate (Step O) in dry DMF (2 mL) at rt. After the solution was stirred at rt for 15 hours, it was poured into EtOAc (10 mL) and washed with H2O and brine, and dried over anhydrous MgSO4. Concentration followed by purification by flash chromatography (hexane: EtOAc=2:1) afforded 63.6 mg of the title compound as a colorless glass.

Workup

  1. customTo a 25 mL round bottom flask were placed
  2. customThe flask was evacuated
  3. additionfilled with nitrogen
  4. additionDry DMF (2 mL) was added to the mixture dropwise at 0° C
  5. stirringAfter the solution was stirred at rt for 15 hours
  6. washwashed with H2O and brine
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationConcentration
  9. customfollowed by purification by flash chromatography (hexane: EtOAc=2:1)

Sources & evidence

ORD record
ord-ece6b6a819144315a5c4f3e6eb86b364
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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