Benzyl Bromide → HCID 118159485, Verbindung

HRID 628444Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 628444
[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[C:9]([C:11]#[N:12])[NH:10][C:5]2=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C.CCOC(C)=O>[CH2:19]([N:10]1[C:5]2[C:6](=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:8]=[C:9]1[C:11]#[N:12])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 918259655-Chloro-1H-pyrrolo[3,2-b]pyridine-2-carbonitrile

Produkt 1

HCID 118159485HCID 118159485, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5-Chloro-1H-pyrrolo[3,2-b]pyridine-2-carbonitrile (0.10 g, 0.56 mmol, from Step 2) in DMF (1.3 mL) was treated with K2CO3 (0.12 g, 0.84 mmol) and benzyl bromide (74 μL, 0.62 mmol, Aldrich) overnight. The reaction mixture was diluted with EtOAc and washed three times with water and once with brine. The organic layer was dried over sodium sulfate, filtered and concentrated. Flash chromatography, eluting with a gradient from 0-20% EtOAc in hexanes afforded purified product. Yield: (0.12 g, 80%).

Aufarbeitung

  1. washwashed three times with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washFlash chromatography, eluting with a gradient from 0-20% EtOAc in hexanes
  6. customafforded
  7. custompurified product

Quellen und Nachweise

ORD-Eintrag
ord-8fc30a2cfdc0491b89fc78812a03b02e
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309246B2

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