HCID 12146854, compound → 2-(1H-Pyrrolo[3,2-b]pyridin-3-yl)ethanamine

HRID 731590Notes

Reaction equation

HRID 731590 reaction equation
O=[C:2]([C:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[NH:8][CH:7]=1)[C:3]([NH2:5])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[NH2:5][CH2:3][CH2:2][C:6]1[C:10]2[C:9](=[CH:14][CH:13]=[CH:12][N:11]=2)[NH:8][CH:7]=1

Participants

4

Reactant 2

HCID 12146854HCID 12146854, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 121468492-(1H-Pyrrolo[3,2-b]pyridin-3-yl)ethanamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-oxo-2-(1H-pyrrolo[3,2-b]pyridin-3-yl)acetamide (1 eq.) in ether is treated with lithium aluminum hydride (4 eq.), heated at reflux temperature for 8 h, cooled to 0° C., quenched by addition of Rochelle's salt solution and extracted with CH2Cl2. The extracts are combined, dried over MgSO4 and concentrated to afford the title amine, which is used directly in the next step.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 8 h
  3. customquenched by addition of Rochelle's salt solution
  4. extractionextracted with CH2Cl2
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b28922833a2d49e7a273e586d7e6d236
Source dataset
uspto-grants-2009_09
Patent number
US07585876B2

Reaction notes

Loading…