Styrene → (E)-3-methyl-7-styrylquinazolin-4(3H)-one

HRID 1619404Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1619404
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:13])[N:7]([CH3:12])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH2:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CN(C=O)C.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:12][N:7]1[C:6](=[O:13])[C:5]2[C:10](=[CH:11][C:2](/[CH:14]=[CH:15]/[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:3][CH:4]=2)[N:9]=[CH:8]1

Komponenten

9

Edukt 4

HCID 7501StyreneHCID 10796Cesium carbonateHCID 80271Tri-o-tolylphosphineHCID 585745147-Bromo-3-methyl-3,4-dihydroquinazolin-4-one

Produkt 1

HCID 58574275(E)-3-methyl-7-styrylquinazolin-4(3H)-oneAusbeute 33,6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 7-bromo-3-methylquinazolin-4(3H)-one (100 mg, 0.42 mmol), styrene (109 mg, 1.05 mmol), Cs2CO3 (163.8 mg, 0.5 mmol), Bu4NBr (135 mg, 0.42 mmol), tri(o-tolyl)phosphine (128 mg, 0.42 mmol), and Pd(OAc)2 in DMF (5 mL) was stirred at 100° C. for 3 hours. After it was cooled to room temperature, the mixture was diluted with H2O (30 mL) and extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with brine and dried over Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the desired product (37 mg). MS (ESI): 263 (MH+); 1H NMR (300 MHz, DMSO-d6) δ 8.37 (s, 1H), 8.15-8.12 (d, J=8.70 Hz, 1H), 7.85-7.82 (m, 2H), 7.69-7.67 (d, J=7.26 Hz, 2H), 7.57-7.30 (m, 5H), 3.49 (s, 3H).

Aufarbeitung

  1. extractionextracted with ethyl acetate (2×30 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and concentration
  5. customthe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-06d07ab12127429cb85d4555f6d63b54
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772301B2

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