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Dimethylamine, hydrochloride → Dimethyl-(1H-pyrrolo[2,3-b]pyridin-5-ylmethyl)-amine

HRID 269485
Notes
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Reaction equation

HRID 269485 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([CH:10]=O)[CH:9]=[C:4]2[CH:3]=[CH:2]1.Cl.[CH3:13][NH:14][CH3:15].[OH-].[Na+].C([BH3-])#N.[Na+]>CO.O>[CH3:13][N:14]([CH3:15])[CH2:10][C:8]1[CH:9]=[C:4]2[CH:3]=[CH:2][NH:1][C:5]2=[N:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 228320511H-Pyrrolo[2,3-b]pyridine-5-carbaldehyde

Product 1

HCID 59832309Dimethyl-(1H-pyrrolo[2,3-b]pyridin-5-ylmethyl)-amineYield 33%

Reagents, catalysts & solvents 2

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes
HCID 887
Methanol
Solvent
HCID 962WaterSolvent

Procedure

To 1H-Pyrrolo[2,3-b]pyridine-5-carbaldehyde (114 mg, 0.78 mmol), in methanol (10 ml) was added dimethylamine hydrochloride (127 mg, 1.56 mmol, NaOH (31.2 mg, 0.78 mmol), sodium cyanoborohydride (49 mg, 0.78 mmol) and the solution was stirred under nitrogen for 12 hr. Poured into water (50 mL), extracted with ethyl acetate, dried (Na2SO4) to afforded Dimethyl-(1H-pyrrolo[2,3-b]pyridin-5-ylmethyl)-amine (44 mg, 33% yield) used without purification. MS: m/e 176.1 (M+H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-40b9bc0a873a44b18533dfd18f6659b6
Source dataset
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07446199B2

Reaction notes

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