m-Xylyl bromide → 3-(3,4-Dimethyl-benzoyl)-1-(3-methyl-benzyl)-2,3-dihydro-1H-quinolin-4-one

HRID 226938

Reaktionsgleichung

Reaktionsgleichung von HRID 226938
[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].[CH3:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28]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]([CH2:24][C:25]2[CH:32]=[CH:31][CH:30]=[C:27]([CH3:28])[CH:26]=2)[CH2:10]1)=[O:8]

Komponenten

5

Edukt 3

HCID 12099m-Xylyl bromideHCID 24758Sodium hydrideHCID 577545153-(3,4-Dimethyl-benzoyl)-1H-quinolin-4-one

Produkt 1

HCID 670721353-(3,4-Dimethyl-benzoyl)-1-(3-methyl-benzyl)-2,3-dihydro-1H-quinolin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Compound 4m was prepared following the procedure outlined in Step 3 of Example 1 using 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, 3 mL of anhydrous dimethylformamide, and 74.0 mg (0.40 mmol) of 3-methylbenzylbromide. The crude product 4m was purified by flash chromatograph to yield 55 mg of colorless solid: LC-MSD, m/z for C26H23NO2, [M+H]+: 382.5, [M+H]+: 383.5; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=2.628 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.3-2.4 (t, 9H), 5.4 (s, 2H), 7.0 (d, 2H), 7.12 (d, 1H), 7.18 (d, 1H), 7.25 (d, 1H), 7.4 (t, 2H), 7.58 (m, 2H), 7.65 (s, 1H), 8.26 (s, 1H), 7.48 (s, 1H).

Aufarbeitung

  1. customThe crude product 4m was purified by flash chromatograph

Quellen und Nachweise

ORD-Eintrag
ord-d1cbefff430f4df5b2e42ab307128bfc
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557213B2

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