HCID 86667167, compound → HCID 67980763, compound

HRID 1260160Notes

Reaction equation

HRID 1260160 reaction equation
Br[CH:2]1[C:11]2[C:6]3=[C:7]([C:12]([C:14](=[O:20])[C:15]([O:17][CH2:18]C)=[O:16])=[CH:13][N:5]3[CH2:4][CH2:3]1)[CH:8]=[CH:9][CH:10]=2>CN(C)C=N.C([O-])(=O)C.[Ag+]>[CH3:18][O:17][C:15](=[O:16])[C:14]([C:12]1[C:7]2=[C:6]3[C:11](=[CH:10][CH:9]=[CH:8]2)[CH:2]([O:17][C:15](=[O:16])[CH3:14])[CH2:3][CH2:4][N:5]3[CH:13]=1)=[O:20]

Participants

4

Reactant 1

HCID 86667167HCID 86667167, compound

Product 1

HCID 67980763HCID 67980763, compound

Reagents, catalysts & solvents 2

HCID 11246Silver acetateCatalystHCID 12669390N,N-DimethylmethanimidamideSolvent

Procedure

To a solution of ethyl (6-bromo-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)(oxo)acetate (890 mg, 2.76 mmol) in dimethylformamidine (20 mL) at 0° C. was added silver acetate (458 mg, 2.76 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 2 hr. The mixture was filtered through Celite and rinsed with ethyl acetate (100 mL). The filtrated was diluted with water (100 mL) and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed saturated aqueous sodium chloride solution (50 mL) dried over anhydrous sodium sulfate, and evaporated to dryness. The residue was purified by silica gel chromatography, eluting with a ethyl acetate/hexanes (10-60%) to methyl[6-(acetyloxy)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl](oxo)acetate as a yellow solid (326 mg, 39%). Mp: 165-168° C.; 1H NMR (CDCl3) 400 MHz δ: 8.39 (s, 1H), 8.29 (d, J=7.4 Hz, 1H), 7.31-7.36 (m, 2H), 6.22 (t, J=3.5 Hz, 1H), 4.33-4.36 (m, 2H), 4.41-4.43 (m, 1H), 3.95 (s, 3H), 2.44-2.47 (m, 1H), 2.36-2.39 (m, 1H); LCMS [M+H]: 302.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washrinsed with ethyl acetate (100 mL)
  3. additionThe filtrated was diluted with water (100 mL)
  4. extractionextracted with ethyl acetate (3×100 mL)
  5. washThe combined organic layers were washed saturated aqueous sodium chloride solution (50 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated to dryness
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with a ethyl acetate/hexanes (10-60%) to methyl[6-(acetyloxy)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl](oxo)acetate as a yellow solid (326 mg, 39%)

Sources & evidence

ORD record
ord-8acc851f46b3449c8d5e02ad50cd8df3
Source dataset
uspto-grants-2013_06
Patent number
US08470786B2

Reaction notes

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