m-Xylyl bromide → 3-Benzoyl-1-(3-methyl-benzyl)-1H-quinolin-4-one

HRID 226942

Reaktionsgleichung

Reaktionsgleichung von HRID 226942
[H-].[Na+].[C:3]([CH:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH2:12]1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]Br>CN(C)C=O>[C:3]([C:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH2:22][C:23]2[CH:30]=[CH:29][CH:28]=[C:25]([CH3:26])[CH:24]=2)[CH:12]=1)(=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 12099m-Xylyl bromideHCID 24758Sodium hydrideHCID 668960903-benzoyl-2,3-dihydro-1H-quinolin-4-one

Produkt 1

HCID 21368463-Benzoyl-1-(3-methyl-benzyl)-1H-quinolin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Compound 4t was prepared following the procedure outlined in Step 3 of Example 1 using 16 mg (0.4 mmol) of sodium hydride (60%), 75 mg (0.31 mmol) of 3-benzoyl-2,3-dihydro-1H-quinolin-4-one 3e, 3 mL of anhydrous dimethylformamide, 75.6 mg (0.40 mmol) of 3-methylbenzylbromide. The crude product 4t was purified by flash chromatography to yield 45 mg of colorless solid: LC-MSD, m/z for C24H19NO2, [M+H]+=354.4, [M+2H]+=355.4; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=2.146 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.35 (s, 3H), 5.38 (s, 2H), 7.00 (d, 2H), 7.33 (d, 1H), 7.22-7.26 (m, 1H), 7.36-7.45 (m, 4H), 7.50-7.60 (m, 2H), 7.82-7.86 (m, 2H), 8.31 (s, 1H), 8.44-8.48 (m, 1H).

Aufarbeitung

  1. customThe crude product 4t was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ef3d7ab182b44d6d9539b34f5d0f942f
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557213B2

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