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

HRID 1404611Notes

Reaction equation

HRID 1404611 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-5e8db0f63f75499cbb5ce68fc1a480ba
Source dataset
uspto-grants-2014_12
Patent number
US08912330B2

Reaction notes

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