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Cesium carbonate → HCID 86679614, Verbindung

HRID 577668
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 577668
Cl[C:2]1[N:3]=[C:4]([O:19][C:20]2[CH:21]=[C:22]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH:23]=[CH:24][CH:25]=2)[C:5]2[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=2[N:7]=1.[CH3:34][N:35]([CH3:44])[CH2:36][CH2:37][N:38]1[CH:42]=[C:41]([NH2:43])[CH:40]=[N:39]1.C([O-])([O-])=O.[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.[Cl-].[Na+].O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:29]([O:28][C:27](=[O:33])[NH:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([O:19][C:4]2[C:5]3[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=3[N:7]=[C:2]([NH:43][C:41]3[CH:40]=[N:39][N:38]([CH2:37][CH2:36][N:35]([CH3:44])[CH3:34])[CH:42]=3)[N:3]=2)[CH:21]=1)([CH3:32])([CH3:31])[CH3:30]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 283739571-(2-(Dimethylamino)ethyl)-1H-pyrazol-4-amineHCID 86679612tert-butyl (3-((2-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)phenyl)carbamate

Produkt 1

HCID 86679614
HCID 86679614, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a solution of tert-butyl {3-[(2-chloro-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy]phenyl}carbamate (300 mg, 0.61 mmol) in 1,4-dioxane (4 mL) in a microwave vial was added 1-[2-(dimethylamino)ethyl]-1H-pyrazol-4-amine (94.1 mg, 0.61 mmol) followed by Cs2CO3 (298 mg, 0.915 mmol), Pd2(dba)3 (8.2 mg, 0.009 mmol) and Xantphos (5.4 mg, 0.009 mmol) and the mixture heated in the microwave to 140° C. for 45 min. The reaction was cooled to rt and brine (20 mL) was added and the mixture was extracted with EtOAc (three×10 mL). The combined extracts were dried over MgSO4, filtered and stripped to give the title compound as a dark oil that was taken on to the next step with no purification. m/z (ESI+) for C30H44N8O4Si 609.25 (M+H)+.

Aufarbeitung

  1. temperatureThe reaction was cooled to rt
  2. extractionthe mixture was extracted with EtOAc (three×10 mL)
  3. dry with materialThe combined extracts were dried over MgSO4
  4. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-343c49ba68d946238ebe8bda71a4f65b
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09040547B2

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