Trimethylsilylacetylene → 6-ethynyl-3,4-dihydroquinolin-2(1H)-one

HRID 1649732Notes

Reaction equation

HRID 1649732 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.C[Si]([C:17]#[CH:18])(C)C>N1C=CC=CC=1.C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:17]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2)#[CH:18]

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 143732816-Bromo-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 143732916-ethynyl-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 8.0 g of 6-bromo-3,4-dihydrocarbostyril, 6.95 g of trimethylsilylacetylene, 460 mg of bis(triphenylphosphine)palladium dichloride and 62 mg of cuprous iodide in 53 ml of pyridine and 11 ml of triethylamine was refluxed for 3 days. The solvent was removed under reduced pressure, 50 ml of methanol added along with 300 mg of potassium carbonate, and the mixture stirred under nitrogen for 18 hours. The solvent was removed under reduced pressure and the residue chromatographed on silica gel, eluting with 3% methanol in methylene chloride, giving a product of 6-ethynyl-3,4-dihydrocarbostyril, m.p. 182°-184° C.

Workup

  1. temperaturewas refluxed for 3 days
  2. customThe solvent was removed under reduced pressure, 50 ml of methanol
  3. additionadded along with 300 mg of potassium carbonate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue chromatographed on silica gel
  6. washeluting with 3% methanol in methylene chloride

Sources & evidence

ORD record
ord-17bffcf3516e4361ac12c9fcfdf6bcef
Source dataset
uspto-grants-1990_05
Patent number
US04921862

Reaction notes

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