Sodium Carbonate → HCID 178489343, Verbindung

HRID 2196568Notizen

Reaktionsgleichung

CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([CH:32]=[CH:33][CH:34]=2)[CH2:12][N:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:14][CH2:15][N:16]([CH3:24])C(=O)OC(C)(C)C)O1.Br[C:37]1[CH:53]=[C:52]([CH3:54])[C:40]2[NH:41][C:42]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=3[O:50][CH3:51])=[N:43][C:39]=2[CH:38]=1.[C:55](=[O:58])([O-])[O-:56].[Na+].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:51][O:50][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=1[C:42]1[NH:41][C:40]2[C:52]([CH3:54])=[CH:53][C:37]([C:9]3[CH:10]=[C:11]([CH:32]=[CH:33][CH:34]=3)[CH2:12][N:13]([CH2:14][CH2:15][NH:16][CH2:24][C:55]([O:56][C:11]([CH3:32])([CH3:12])[CH3:10])=[O:58])[C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[CH:38][C:39]=2[N:43]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of 158 (0.165 g, 0.336 mmol) in DME (1.5 mL) and water (0.5 mL) was added 159 (0.107 g, 0.336 mmol), sodium carbonate (0.107 g, 1.009 mmol) followed by Pd(Ph3P)4 (0.025 g, 0.022 mmol). The reaction mixture was degassed with nitrogen and heated to 80° C. for 16 hours. After the usual work-up the crude material was purified by silica gel chromatography (Biotage 25M, 20 to 30 to 50% ethyl acetate in hexanes) to give 160 (97.7 mg, 0.163 mmol, 48.3% yield) as yellow crusty solid. LRMS (ESI): (calc.) 600.7 (found) 601.5 (MH)+.

Aufarbeitung

customThe reaction mixture was degassed with nitrogen
customAfter the usual work-up the crude material was purified by silica gel chromatography (Biotage 25M, 20 to 30 to 50% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-0cd01431ac83472a80fa748e2e439786
Quelldatensatz: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08338437B2

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