Sodium hydride → 3-(3,4-dimethyl-benzoyl)-1-(2-fluoro-benzyl)-2,3-dihydro-1H-quinolin-4-one

HRID 226937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 226937
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:7]([C:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)=[O:8].[F:24][C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[CH2:27]Br>CN(C)C=O>[CH3:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:7]([CH:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:27][C:26]2[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=2[F:24])[CH2:10]1)=[O:8]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 67968alpha-Bromo-o-fluorotolueneHCID 577545153-(3,4-Dimethyl-benzoyl)-1H-quinolin-4-one

Produkt 1

HCID 668968333-(3,4-dimethyl-benzoyl)-1-(2-fluoro-benzyl)-2,3-dihydro-1H-quinolin-4-oneAusbeute 20,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In 3 mL of anhydrous dimethylformamide was suspended 16 mg (0.4 mmol) of sodium hydride (60%), 86 mg (0.31 mmol) of 3-(3,4-dimethyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one 3a was added and the mixture was stirred at rt. After 30 minutes, 75.6 mg (0.40 mmol) of 2-fluorobenzylbromide was added and the reaction was stirred at room temperature for 1 hour. The reaction mixture was quenched by the addition of 10 mL of water. The crude product precipitated out were isolated by filtration and purified by flash chromatography to yield 25 mg of colorless solid 41: LC-MSD, m/z for C25H20FNO2 [M+H]+=386.4, [M+2H]+=387.4; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=2.526 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.2-2.3 (d, 6H), 5.7 (s, 2H), 7.1-7.3 (m, 4H), 7.3-7.4 (m, 1H), 7.4-7.5 (m, 2H),7.54 (s, 1H), 7.6-7.66 (d, 1H), 7.67-7.74 (t, 1H), 8.2 (d, 1H), 8.58 (s, 1H).

Aufarbeitung

  1. additionwas added
  2. stirringthe reaction was stirred at room temperature for 1 hour
  3. customThe reaction mixture was quenched by the addition of 10 mL of water
  4. customThe crude product precipitated out
  5. customwere isolated by filtration
  6. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ac7ee47fca1d44daa19fbcd6fd68c2ee
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557213B2

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