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Sodium borohydride → N-(2,6-dichloro-3-fluorobenzyl)-6-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]-1H-pyrrolo[3,2-b]pyridin-1-amine

HRID 1404617
Notes
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Reaction equation

HRID 1404617 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1/[CH:10]=[N:11]/[N:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[CH:22]=[N:23][N:24]([CH:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)[CH:25]=3)[CH:19]=2)[CH:14]=[CH:13]1.[BH4-].[Na+]>CO.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH2:10][NH:11][N:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[CH:22]=[N:23][N:24]([CH:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)[CH:25]=3)[CH:19]=2)[CH:14]=[CH:13]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 87408679(E)-1-(2,6-dichloro-3-fluorophenyl)-N-[6-(1-piperidin-4-ylpyrazol-4-yl)pyrrolo[3,2-b]pyridin-1-yl]methanimine

Product 1

HCID 46235049N-(2,6-dichloro-3-fluorobenzyl)-6-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]-1H-pyrrolo[3,2-b]pyridin-1-amine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 516892
Sodium Bicarbonate
Solvent

Procedure

A solution of N-[(E)-(2,6-dichloro-3-fluorophenyl)methylidene]-6-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]-1H-pyrrolo[3,2-b]pyridin-1-amine (35 mg, 0.063 mmol) in MeOH (5 mL) was treated with excess amount of NaBH4 under reflux. HPLC check indicated disappearance of the starting material. The mixture was diluted with aqueous NaHCO3, and extracted with ethyl acetate. The organic solution was dried and evaporated.

Workup

  1. temperatureunder reflux
  2. extractionextracted with ethyl acetate
  3. customThe organic solution was dried
  4. customevaporated

Sources & evidence

ORD record
ord-2fbef017c0b84551a515acbfbcf9c299
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08912330B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes