Tributyltin Chloride → HCID 67117498, Verbindung

HRID 1924918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1924918
[C:1]([O:5][C:6](=[O:31])[N:7]([C:21]1[C:22]2[N:23]([CH:28]=[CH:29][N:30]=2)[C:24](Br)=[CH:25][N:26]=1)[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C([Mg]Cl)(C)C.[CH2:37]([Sn:41](Cl)([CH2:46][CH2:47][CH2:48][CH3:49])[CH2:42][CH2:43][CH2:44][CH3:45])[CH2:38][CH2:39][CH3:40]>C1COCC1>[NH3:7].[C:1]([O:5][C:6](=[O:31])[N:7]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)[C:21]1[C:22]2[N:23]([CH:28]=[CH:29][N:30]=2)[C:24]([Sn:41]([CH2:42][CH2:43][CH2:44][CH3:45])([CH2:46][CH2:47][CH2:48][CH3:49])[CH2:37][CH2:38][CH2:39][CH3:40])=[CH:25][N:26]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 15096Tributyltin ChlorideHCID 86616747HCID 86616747, VerbindungHCID 178418918HCID 178418918, Verbindung

Produkt 2

HCID 222AmmoniaHCID 67117498HCID 67117498, VerbindungAusbeute 148 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

In the same way as described for Compound 212, step 2, using a solution of (5-bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-carbamic acid tert-butyl ester (0.3 g, 0.62 mmol) in THF (5 mL), and isopropylmagnesium chloride (0.46 mL of a 2M solution in THF, 0.67 mmol). After stirring for 5 min, tributyltin chloride (0.28 mL, 1.04 mmol) is added and the reaction is stirred at −78° C. for 10 min before being allowed to warm to room temperature. After stirring at room temperature for 30 min, the mixture is concentrated. The crude mixture is purified by silica gel flash column chromatography using 95:5 DCM:NH3 (7M in MeOH), to give [4-(4-methyl-piperazin-1-yl)-phenyl]-(5-tributylstannanyl-imidazo[1,2-a]pyrazin-8-yl)-carbamic acid tert-butyl ester (0.32 g, 70%) as a yellow oil. LCMS: Rt 7.03 min (92.3%), m/z (ES+) 695, 697, 699.

Aufarbeitung

  1. stirringthe reaction is stirred at −78° C. for 10 min
  2. stirringAfter stirring at room temperature for 30 min
  3. concentrationthe mixture is concentrated
  4. customThe crude mixture is purified by silica gel flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c74940a3da7040aea8bd2b9e942167ac
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178530B2

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