Triethylamine → N-(4-(7-((2-tert-butoxypyridin-4-yl)ethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide

HRID 1188262Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1188262
[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:24])[C:8]([C:13]3[CH:18]=[CH:17][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][CH:14]=3)=[CH:9][O:10]2)=[CH:5][CH:4]=1)#[CH:2].Br[C:26]1[CH:31]=[CH:30][N:29]=[C:28]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>O1CCCC1.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.[Cu](I)I>[C:33]([O:32][C:28]1[CH:27]=[C:26]([C:2]#[C:1][C:3]2[CH:12]=[C:11]3[C:6]([C:7](=[O:24])[C:8]([C:13]4[CH:18]=[CH:17][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][CH:14]=4)=[CH:9][O:10]3)=[CH:5][CH:4]=2)[CH:31]=[CH:30][N:29]=1)([CH3:36])([CH3:34])[CH3:35]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 457878724-Bromo-2-tert-butoxypyridineHCID 86695056N-(4-(7-ethynyl-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide

Produkt 1

HCID 86695057N-(4-(7-((2-tert-butoxypyridin-4-yl)ethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

N-(4-(7-ethynyl-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide (100 mg, 0.29 mmol) was combined with 4-bromo-2-tert-butoxypyridine (0.074 mg, 1.1 eq), PdCl2(PPh3)2 (10 mg, 0.05 eq), copper iodide (4 mg 0.002 eq), triphenylphosphine (6 mg 0.03 eq) and triethylamine (0.12 ml, 4.0 eq) in dry tetrahydrofuran (10 ml) and heated in microwave for 30 minutes at 85° C. Solvent was removed from the product under reduced pressure, and the residue was extracted with ethyl acetate in the presence of water. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford N-(4-(7-((2-tert-butoxypyridin-4-yl)ethynyl)-4-oxo-4H-chromen-3-yl)phenyl)methanesulfonamide. This crude product was dissolved in dichloromethane/trifluoroacetic acid 1:1 (4 ml) and stirred at room temperature for 1 hour. The solvent was removed under reduced pressure, and the residue was extracted with ethyl acetate in the presence of water. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The product was heated in acetonitrile, cooled, and the solids were filtered out. This procedure was repeated twice in order to afford N-(4-(4-oxo-7-((2-oxo-1,2-dihydropyridin-4-yl)ethynyl)-4H-chromen-3-yl)phenyl)methanesulfonamide.

Aufarbeitung

  1. customSolvent was removed from the product under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate in the presence of water
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c9fdb1569ef44975bd1c3b12bfbbb046
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673966B2

Notizen zur Reaktion

Wird geladen…