HCID 58065823, Verbindung → HCID 71253947, Verbindung

HRID 1028314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1028314
[CH3:1][Mg]Br.[Br:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH2:19][C:20](=[O:29])[CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][C:13]([Br:18])=[CH:12][CH:11]=3>C1COCC1>[Br:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH2:19][C:20]([CH3:1])([OH:29])[CH2:21][O:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][C:13]([Br:18])=[CH:12][CH:11]=3

Komponenten

4

Edukt 2

HCID 58065823HCID 58065823, VerbindungHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 71253947HCID 71253947, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methylmagnesium bromide (92 μl, 3.0 M in THF) was added to an ice-cooled solution of title compound of example 103, step 1, 1-(3,6-dibromo-9H-carbazol-9-yl)-3-phenoxypropan-2-one (86 mg, 0.18 mmol) in anhydrous THF (1.8 ml). The reaction was stirred in the gently warming ice bath for 6 hours, and then quenched by addition of water. The crude mixture was diluted with EtOAc and washed with saturated sodium bicarbonate, water and then brine. The organic layer was dried over Na2SO4, filtered and condensed. Some unreacted starting material was precipitated from ˜50% acetone/hexanes. The condensed filtrate was carried forward. Yield=89%. MS (ESI), m/z: calculated 486.98. found 531.7 (M+HCOO−).

Quellen und Nachweise

ORD-Eintrag
ord-021ddd86244c404186117e2ea045e6a4
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735440B2

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