Water → HCID 58386693, Verbindung

HRID 74679Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 74679
C[Si](C)(C)[C:3]#[C:4][CH2:5][OH:6].[F:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([C:19]([C:21]1[CH:26]=[C:25]([N:27]3[CH2:32][CH2:31][CH:30]([N:33]4[C:41]5[C:36](=[N:37][CH:38]=[CH:39][CH:40]=5)[NH:35][C:34]4=[O:42])[CH2:29][CH2:28]3)[C:24](I)=[CH:23][N:22]=1)=[O:20])[CH2:14][CH2:13]2.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCOCC1.C1COCC1.[Cu]I>[F:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([C:19]([C:21]1[CH:26]=[C:25]([N:27]3[CH2:32][CH2:31][CH:30]([N:33]4[C:41]5[C:36](=[N:37][CH:38]=[CH:39][CH:40]=5)[NH:35][C:34]4=[O:42])[CH2:29][CH2:28]3)[C:24]([C:3]#[C:4][CH2:5][OH:6])=[CH:23][N:22]=1)=[O:20])[CH2:14][CH2:13]2

Komponenten

8

Edukt 4

HCID 962WaterHCID 789302-Propyn-1-ol, 3-(trimethylsilyl)-HCID 2724141Tetrabutylammonium FluorideHCID 583867541-[2'-(5-fluoro-2,3-dihydro-indole-1-carbonyl)-5'-iodo-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-4-yl]-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

Produkt 1

HCID 58386693HCID 58386693, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Under an argon atmosphere 44 mg (0.34 mmol) 3-trimethylsilanyl-prop-2-yn-1-ol, 50 μL TEA, 13 mg 1,1′-bis(diphenylphosphine)ferrocene dichloropalladium (II) and 3 mg (20 μmol) copper(I) iodide were added to 0.10 g (0.17 mmol) 1-[2′-(5-fluoro-2,3-dihydro-indole-1-carbonyl)-5′-iodo-3,4,5,6-tetrahydro-2H-[1,4′]bipyridinyl-4-yl]-1,3-dihydro-imidazo[4,5-b]pyridin-2-one in 4.0 mL 1,4-dioxane. Then 0.36 mL (0.36 mmol) of a 1 molar tetrabutylammonium fluoride solution in THF were added dropwise and the mixture was then stirred for 4 h at 80° C. The reaction mixture was mixed with water and the precipitate formed was suction filtered. The precipitate was stirred in 6 mL DMF and suction filtered. The filtrate was purified by preparative HPLC-MS. The product-containing fractions were combined and freeze-dried.

Aufarbeitung

  1. customthe precipitate formed
  2. filtrationfiltered
  3. stirringThe precipitate was stirred in 6 mL DMF
  4. filtrationsuction filtered
  5. customThe filtrate was purified by preparative HPLC-MS
  6. customfreeze-dried

Quellen und Nachweise

ORD-Eintrag
ord-5c313052bd85448db9a0437b0f8e8a0b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829006B2

Notizen zur Reaktion

Wird geladen…