m-Xylyl bromide → 3-(3,4-dimethyl-benzoyl)-6-fluoro-1-(3-methyl-benzyl)-1H-quinolin-4-one

HRID 226964

Reaktionsgleichung

[CH3:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[CH3:22])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:18])[CH:14]=2)[NH:9][CH:8]=1)=[O:6].C[Si](C)(C)[N-][Si](C)(C)C.[K+].[CH3:33][C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=1)[CH2:37]Br>O1CCCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[CH3:22])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:18])[CH:14]=2)[N:9]([CH2:33][C:34]2[CH:41]=[CH:40][CH:39]=[C:36]([CH3:37])[CH:35]=2)[CH:8]=1)=[O:6]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

Compound 4uu was prepared following the procedure outlined in Step 3 of Example 1. Briefly described here, 0.050 g (0.169 mmol) of 3-(3,4-dimethyl-benzoyl)-6-fluoro-1H-quinolin-4-one 3j, 0.4 mL of potassium hexamethyldisilazide (0.5 M in toluene, 0.203 mmol) and 37.6 mg (0.203 mmol) of 3-methylbenzyl bromide were combined in 1.5 mL of tetrahydrofuran and heated at 60° C. for 3 h. Purification of the crude product using flash chromatography (30-50% ethyl acetate in hexane) yielded 52.2 mg of 3-(3,4-dimethyl-benzoyl)-6-fluoro-1-(3-methyl-benzyl)-1H-quinolin-4-one as a white solid 4uu: LC-MSD, m/z for C26H22FNO2, [M+H]=400.5; Reverse phase HPLC gradient, 20-95% acetonitrile with 0.1% TFA in 4 minutes, retention time=2.9 min; 1H NMR (400 MHz, CDCl3): δ 8.26 (1H, s), 8.11 (1H, m), 7.64 (1H, s), 7.56 (1H, m), 7.38 (1H, m), 7.32-7.23 (2H, m), 7.18 (1H, m), 7.15 (1H, m), 6.97 (2H, m), 5.37 (2H, s), 2.33 (3H, s), 2.32 (3H, s), 2.31 (3H, s).

Aufarbeitung

customCompound 4uu was prepared
customPurification of the crude product

Quellen und Nachweise

ORD-Eintrag: ord-be70811647bd42f78515e1db5b8d4303
Quelldatensatz: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07557213B2

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