Dimethylamine, hydrochloride → N,N-Dimethyl-1H-pyrrolo[2,3-b]pyridine-5-methanamine

HRID 269485Notes

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

Participants

7

Reactant 4

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

Product 1

HCID 59832309N,N-Dimethyl-1H-pyrrolo[2,3-b]pyridine-5-methanamineYield 33%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 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
Patent number
US07446199B2

Reaction notes

Loading…