HCID 68554750, compound → HCID 57985938, compound

HRID 1869196Notes

Reaction equation

HRID 1869196 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][O:10][C:11](=[O:30])[C:12](=[CH:20][C:21]1[C:25]2=[N:26][CH:27]=[CH:28][CH:29]=[C:24]2[NH:23][CH:22]=1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>C1COCC1>[CH3:9][O:10][C:11](=[O:30])[CH:12]([CH:20]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:21]1[C:25]2=[N:26][CH:27]=[CH:28][CH:29]=[C:24]2[NH:23][CH:22]=1)[C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 68554750HCID 68554750, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 57985938HCID 57985938, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a RT solution of PhMgBr (1 M in THF, 6.5 mL) in THF (10 mL) was added a solution of 2-(1H-pyrrolo[3,2-b]pyridin-3-yl-methylene)-malonic acid tert-butyl ester methyl ester in THF (15 mL) dropwise. After stirring the mixture for 1 hour at RT, the reaction was quenched by addition of water. The diluted mixture was neutralized by addition of HCl (I M) to pH 7 and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (hexane/EtOAc) affording 2-[Phenyl-(1H-pyrrolo[3,2-b]pyridin-3-yl)-methyl]-malonic acid tert-butyl ester methyl ester (680 mg, 69% yield).

Workup

  1. customthe reaction was quenched by addition of water
  2. additionThe diluted mixture was neutralized by addition of HCl (I M) to pH 7
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified via flash chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-c610c8e12a7e477591bd9baf8e7cf3e7
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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