Lithium Hexamethyldisilazide → 4-[(3-fluoro-6-methylphenanthridin-5(6H)-yl)carbonyl]benzene-1,3-diol

HRID 731994Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 731994
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([CH:12]([CH3:28])[N:13]([C:16](=[O:27])[C:17]4[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][C:18]=4[O:25]C)[C:14]=2[CH:15]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3.FC1C=C(F)C=CC=1C1C=CC=CC=1C(NC(=O)C1C=CC(OC)=CC=1OC)C.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11]([CH:12]([CH3:28])[N:13]([C:16]([C:17]4[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]=4[OH:25])=[O:27])[C:14]=2[CH:15]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3

Komponenten

5

Edukt 3

HCID 2733832Lithium HexamethyldisilazideHCID 688162733-Fluoro-5-(2,4-dimethoxybenzoyl)-6-methyl-5,6-dihydrophenanthridineHCID 68816650N-[1-(2',4'-difluoro-1,1'-biphenyl-2-yl)ethyl]-2,4-dimethoxybenzamide

Produkt 1

HCID 115303814-[(3-fluoro-6-methylphenanthridin-5(6H)-yl)carbonyl]benzene-1,3-diolAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-fluoro-5-(2,4-dimethoxybenzoyl)-6-methyl-5,6-dihydrophenanthridine—The title compound was prepared from N-[1-(2′,4′-difluoro-1,1′-biphenyl-2-yl)ethyl]-2,4-dimethoxybenzamide (1.29 g, 3.2 mmol), anhydrous THF (10 mL), and lithium bis(trimethylsilyl)amide (4.0 mL, 1M in THF) according to the procedure and in the same manner as described in Example 33, step d. The resulting residue was purified by flash column chromatography (Biotage® 40 Mi, 30-50% methyl tert-butylether in hexane) affording 1.2 g (99%) of the desired product. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.16 (d, J=6.76 Hz, 3 H) 3.79 (br m, 6 H) 3.92 (s, 1 H) 6.28 (s, 1 H) 6.62 (m, 1H) 7.06 (s, 1 H) 7.34 (br m, 1 H) 7.42 (br m, 3 H) 7.52 (br d, J=7.54 Hz, 1 H) 7.96 (m, 2 H); MS (ESI) m/z 378 ([M+H]+); HRMS: calcd for C23H20FNO3, 377.1427 (M), 378.15000 ([M+H]+); found (ESI_FT), 378.14878

Aufarbeitung

  1. customThe resulting residue was purified by flash column chromatography (Biotage® 40 Mi, 30-50% methyl tert-butylether in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e47b21d3c4a6454ab5d586ca87871ba3
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585871B2

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