Potassium Carbonate → 6-[3-(Imidazol-1-yl)prop-1-yn-1-yl]-3,4-dihydrocarbostyril

HRID 1649741Notes

Reaction equation

HRID 1649741 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.[CH2:13]([N:16]1[CH:20]=[CH:19][N:18]=[CH:17]1)[C:14]#[CH:15].C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.C(N(CC)CC)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:16]1([CH2:13][C:14]#[C:15][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]3)[CH:20]=[CH:19][N:18]=[CH:17]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 125919421-(prop-2-yn-1-yl)-1H-imidazoleHCID 143732816-Bromo-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 143732826-[3-(Imidazol-1-yl)prop-1-yn-1-yl]-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 1049PyridineSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 11.6 mg of cuprous iodide, 86 mg of bis (triphenylphosphine) palladium (II) dichloride, 1.5 g of 6-bromo-3,4-dihydrocarbostyril and 774 mg of N-propargylimidazole was stirred in a mixture of 10 ml of pyridine and 2 ml of triethylamine at 100° C. for 48 hours under nitrogen. The reaction was then treated with 10 ml of saturated aqueous potassium carbonate and extracted with a solution of 10% methanol in methylene chloride. The extract was dried over anhydrous sodium sulfate, the solvent removed under reduced pressure and the residue chromatographed on silica gel eluting with 4% methanol in methylene chloride, yielding 6-[3-(imidazol-1-yl)prop-1-yn-1-yl]-3,4-dihydrocarbostyril, m.p. 164°-168° C.

Workup

  1. extractionextracted with a solution of 10% methanol in methylene chloride
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customthe solvent removed under reduced pressure
  4. customthe residue chromatographed on silica gel eluting with 4% methanol in methylene chloride

Sources & evidence

ORD record
ord-60056c7f9f484636bee78665060a5038
Source dataset
uspto-grants-1990_05
Patent number
US04921862

Reaction notes

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