Triethyl phosphonoacetate → Ethyl 2-(2-(Benzyloxy)-7,8-dihydropyrido[1,2-a]indol-9(6H)-ylidene)acetate

HRID 515740Notes

Reaction equation

HRID 515740 reaction equation
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH2:17]([O:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]1[CH2:34][CH2:35][CH2:36][C:37](=O)[C:29]1=[CH:28]2)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[NH4+].[Cl-]>CN(C=O)C>[CH2:17]([O:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]1[CH2:34][CH2:35][CH2:36][C:37](=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:29]1=[CH:28]2)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 672501482-(Benzyloxy)-7,8-dihydropyrido[1,2-a]indol-9(6H)-one

Product 1

HCID 67249894Ethyl 2-(2-(Benzyloxy)-7,8-dihydropyrido[1,2-a]indol-9(6H)-ylidene)acetateYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of ethyl 2-(diethoxyphosphoryl)acetate (3.11 mL, 15.65 mmol) in DMF (10 mL) was added sodium hydride (60% dispersion in mineral oil) (626 mg, 15.65 mmol) at 0° C. The reaction was slowly warmed to room temperature and stirred for 10 min. 2-(Benzyloxy)-7,8-dihydropyrido[1,2-a]indol-9(6H)-one (570 mg, 1.956 mmol) in DMF was added. The reaction was heated at 65° C. for 2 h, cooled down, poured into saturated NH4Cl aqueous solution, and 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 (608 mg). LCMS m/z=362.5 [M+H]+.

Workup

  1. temperatureThe reaction was heated at 65° C. for 2 h
  2. temperaturecooled down
  3. extractionextracted with ethyl acetate
  4. washThe combined organics were washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3b782bc32de84dcbb41cb007f56d152d
Source dataset
uspto-grants-2015_08
Patent number
US09108969B2

Reaction notes

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