StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Sodium Carbonate → 4-bromo-1-methyl-3-(1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 330996
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 330996
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH3:12])[CH:9]=[C:10](I)[C:3]=12.[CH3:13][N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20](B3OC(C)(C)C(C)(C)O3)[CH:21]=2)[CH2:16][CH2:15]1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.CN(C=O)C.C(Cl)Cl.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH3:12])[CH:9]=[C:10]([C:20]3[CH:21]=[C:22]4[C:17]([CH2:16][CH2:15][N:14]4[CH3:13])=[CH:18][CH:19]=3)[C:3]=12
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 3

HCID 10340Sodium CarbonateHCID 709799671-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolineHCID 710901484-bromo-3-iodo-1-methyl-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 710903864-bromo-1-methyl-3-(1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridineAusbeute 48,8 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 178418476
HCID 178418476, Verbindung
Katalysator
HCID 962WaterLösungsmittel
HCID 6228DimethylformamideLösungsmittel
HCID 6342AcetonitrileLösungsmittel
HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a stirred solution of 4-bromo-3-iodo-1-methyl-1H-pyrrolo[2,3-b]pyridine (D7) (5 g, 14.84 mmol) and 1-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indoline (4.61 g, 17.81 mmol) in ACN (40 mL), DMF (40 mL) and DCM (20 mL) was added 2M sodium carbonate aq. solution (74.2 mL, 148 mmol). Bis(triphenylphosphine)palladium(II) chloride (1.250 g, 1.781 mmol) was then added to the solution and the resulting mixture was heated at 55° C. for ca. 1.5 hour. The reaction mixture was diluted with DCM (100 mL) and water (150 mL). The organic phase was separated and the aqueous phase was further extracted with DCM (100 mL×3). The combined organics were dried and concentrated. The residue was purified by chromatography on silica, eluting with a gradient of 0-20% ethyl acetate in cyclohexane. The corresponding fractions were combined and concentrated to give the title compound (2.48 g). LCMS (A): m/z (M+H)+ 342/344, C17H16BrN3 requires 341/343 (acidic).

Aufarbeitung

  1. customThe organic phase was separated
  2. extractionthe aqueous phase was further extracted with DCM (100 mL×3)
  3. customThe combined organics were dried
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica
  6. washeluting with a gradient of 0-20% ethyl acetate in cyclohexane
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b072d1a30e0442cf89e12e65e6d0669e
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08877742B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion