Triethyl phosphonoacetate → HCID 67249397, compound

HRID 515730Notes

Reaction equation

HRID 515730 reaction equation
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH3:17][O:18][C:19]1[CH:27]=[CH:26][C:25]2[N:24]3[CH2:28][CH2:29][C:30](=O)[C:23]3=[CH:22][C:21]=2[C:20]=1[CH3:32].[NH4+].[Cl-]>CN(C=O)C>[CH3:17][O:18][C:19]1[CH:27]=[CH:26][C:25]2[N:24]3[CH2:28][CH2:29][C:30](=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:23]3=[CH:22][C:21]=2[C:20]=1[CH3:32]

Participants

6

Reactant 4

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 672497037-Methoxy-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-one

Product 1

HCID 67249397HCID 67249397, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of ethyl 2-(diethoxyphosphoryl)acetate (1.38 mL, 6.97 mmol) in DMF (2 mL) was added sodium hydride (60% dispersion in mineral oil) (279 mg, 6.97 mmol) at 0° C. The reaction mixture was stirred for 10 min, then 7-methoxy-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-one (500 mg, 2.323 mmol) in DMF (6 mL) was added. The reaction mixture was warmed to room temperature and stirred for 1 h, then heated at 60° C. for 1 h, cooled down, poured into saturated NH4Cl aqueous solution, extracted with ethyl acetate. The combined organics were washed with water, dried over anhydrous Na2SO4, and concentrated. The residue was purified by silica gel column chromatography to give the title compound (361 mg). LCMS m/z=286.2 [M+H]+.

Workup

  1. stirringstirred for 1 h
  2. temperatureheated at 60° C. for 1 h
  3. temperaturecooled down
  4. extractionextracted with ethyl acetate
  5. washThe combined organics were washed with water
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-eaaf330fbb24494b89c9cc983861df88
Source dataset
uspto-grants-2015_08
Patent number
US09108969B2

Reaction notes

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