Sodium borohydride → tert-butyl 4-{4-[1-(benzylamino)-1H-pyrrolo[3,2-b]pyridin-6-yl]-1H-pyrazol-1-yl}piperidine-1-carboxylate

HRID 1404611Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1404611
[C:1]1(/[CH:7]=[N:8]/[N:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[CH:19]=[N:20][N:21]([CH:23]5[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]5)[CH:22]=4)[CH:16]=3)[CH:11]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO.C([O-])(O)=O.[Na+]>[CH2:7]([NH:8][N:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[N:20][N:21]([CH:23]4[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH2:28]4)[CH:22]=3)[CH:16]=2)[CH:11]=[CH:10]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 58532304tert-butyl 4-[4-[1-[(E)-benzylideneamino]pyrrolo[3,2-b]pyridin-6-yl]pyrazol-1-yl]piperidine-1-carboxylate

Produkt 1

HCID 67458095tert-butyl 4-{4-[1-(benzylamino)-1H-pyrrolo[3,2-b]pyridin-6-yl]-1H-pyrazol-1-yl}piperidine-1-carboxylateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl 4-[4-(1-{[(E)-phenylmethylidene]amino}-1H-pyrrolo[3,2-b]pyridin-6-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate (200 mg, 0.43 mmol) in MeOH (10 mL) was treated with excess amount of NaBH4 under reflux. HPLC check indicates disappearance of the starting material. The mixture was diluted with aqueous NaHCO3, and extracted with ethylacetate. The product was purified by column chromatography (EtOAc:MeOH=100:5) and the entitled intermediate was isolated as a white solid (180 mg, yield 90%).

Aufarbeitung

  1. temperatureunder reflux
  2. extractionextracted with ethylacetate
  3. customThe product was purified by column chromatography (EtOAc:MeOH=100:5)

Quellen und Nachweise

ORD-Eintrag
ord-5e8db0f63f75499cbb5ce68fc1a480ba
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912330B2

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