Benzyl Alcohol → benzyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

HRID 1696218Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1696218
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[C:4]2[NH:11][CH:12]=[CH:13][C:3]=12.[C:14]1([CH2:20]O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.CN(C)CCCN=C=NCC.O>CN(C)C=O>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:9])=[CH:6][N:5]=[C:4]2[NH:11][CH:12]=[CH:13][C:3]=12

Komponenten

6

Edukt 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 260764404-Chloro-1H-pyrrolo(2,3-b)pyridine-5-carboxylic acid

Produkt 1

HCID 57928592benzyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylateAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-Carboxylic acid (343 mg) in N,N-dimethylformamide (4 ml) was added phenylmethanol (375 μl) 4-dimethylaminopyridine (428 mg) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (676 mg). After stirring at ambient temperature for 3 days, the reaction mixture was poured into water, and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by column chromatography on silica gel with chloroform to give benzyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (200 mg) as a yellow powder.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-d5c699157a6d4a7dacb2efe8f337fa7d
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163767B2

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