Hexabutyldistannane → N-tert-butyl-2-(1-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

HRID 246566Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 246566
Br[C:2]1[N:7]=[C:6]2[C:8]([C:19]([NH:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:9][N:10]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]2=[N:4][CH:3]=1.I[C:27]1[C:35]2[C:30](=[N:31][CH:32]=[CH:33][CH:34]=2)[N:29]([CH3:36])[N:28]=1.CCCC[Sn](CCCC)CCCC.CCCC[Sn](CCCC)CCCC>CN(C=O)C.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>[C:22]([NH:21][C:19]([C:8]1[C:6]2=[N:7][C:2]([C:27]3[C:35]4[C:30](=[N:31][CH:32]=[CH:33][CH:34]=4)[N:29]([CH3:36])[N:28]=3)=[CH:3][N:4]=[C:5]2[N:10]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=1)=[O:20])([CH3:25])([CH3:24])[CH3:23]

Komponenten

6

Edukt 3

HCID 6327815HexabutyldistannaneHCID 534706403-Iodo-1-methyl-1H-pyrazolo[3,4-B]pyridineHCID 715756452-bromo-N-(tert-butyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Produkt 1

HCID 71280190N-tert-butyl-2-(1-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamideAusbeute 68,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

To a solution of 2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (400 mg, 936 μmol) and 3-iodo-1-methyl-1H-pyrazolo[3,4-b]pyridine (364 mg, 1.4 mmol) in DMF (8 mL) was added hexabutylditin (814 mg, 709 μL, 1.4 mmol) then the mixture was purged with nitrogen for 10 min. Tetrakis(triphenylphosphine)palladium (0) (54.1 mg, 46.8 μmol) was added and the reaction mixture was heated at 125° C. After 18 h the mixture was filtered through a pad of Celite to remove catalyst, then the filtrates were concentrated in vacuo and purified by chromatography (silica, 10-70% ethyl acetate in hexanes) to obtain N-tert-butyl-2-(1-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (306 mg, 638 μmol, 68%) as an off-white powder. MS (M+H)+=480.

Aufarbeitung

  1. customthe mixture was purged with nitrogen for 10 min
  2. filtrationAfter 18 h the mixture was filtered through a pad of Celite
  3. customto remove catalyst
  4. concentrationthe filtrates were concentrated in vacuo
  5. custompurified by chromatography (silica, 10-70% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-93f7f36ae35e483f8570aef10754e723
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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