Tetrabutylammonium Fluoride → 8-ethynyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

HRID 1970045Notes

Reaction equation

HRID 1970045 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:19]=[C:20]1[C:29]2[NH:30][CH:31]=[CH:32][C:28]=2[C:27]2[CH:26]=[C:25]([C:33]#[C:34][Si](C)(C)C)[CH:24]=[CH:23][C:22]=2[NH:21]1.[CH2:39]([C:41]([O-:43])=[O:42])[CH3:40]>O1CCCC1>[C:33]([C:25]1[CH:24]=[CH:23][C:22]2[NH:21][C:20](=[O:19])[C:29]3[NH:30][CH:31]=[CH:32][C:28]=3[C:27]=2[CH:26]=1)#[CH:34].[CH2:39]([C:41]([O-:43])=[O:42])[CH3:40]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 866275524-oxo-8-trimethylsilanylethynyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

Product 1

HCID 866275508-ethynyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylateYield 50.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.2 ml (1.2 mmol) of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran is added to a solution of 398 mg (1.13 mmol) of 4-oxo-8-trimethylsilanylethynyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in 10 ml of tetrahydrofuran, then the mixture is stirred for 1 hour at room temperature. The solvent is evaporated and the product is extracted with ethyl acetate. The organic phase is washed with a 1M aqueous solution of hydrochloric acid, a saturated solution of sodium chloride, dried over magnesium sulfate, filtered and evaporated. The product is crystallized in a methanol/acetone mixture (4/1) to give 160 mg (50%) of 8-ethynyl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

Workup

  1. customThe solvent is evaporated
  2. extractionthe product is extracted with ethyl acetate
  3. washThe organic phase is washed with a 1M aqueous solution of hydrochloric acid
  4. dry with materiala saturated solution of sodium chloride, dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe product is crystallized in a methanol/acetone mixture (4/1)

Sources & evidence

ORD record
ord-075bb92e6945455e98b0ee340ea52bcb
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

Loading…