Aluminium lithium hydride → 2-(1H-pyrrolo[3,2-c]pyridin-3-yl)ethanamine
Reaction equation
O=[C:2]([C:6]1[C:10]2[CH:11]=[N: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>[NH:8]1[C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[C:6]([CH2:2][CH2:3][NH2:5])=[CH:7]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 2-oxo-2-(1H-pyrrolo[3,2-c]pyridin-3-yl)-acetamide (1 eq.) in ether is treated with lithium aluminum hydride (4 eq.), refluxed for 8 h, cooled to 0° C. and quenched by addition of Rochelle's salt solution. The reaction mixture is extracted with CH2Cl2. The extracts are combined dried over MgSO4 and concentrated in vacuo to give the title amine product, which is used as is in step 9, below.
Workup
- temperaturerefluxed for 8 h
- customquenched by addition of Rochelle's salt solution
- extractionThe reaction mixture is extracted with CH2Cl2
- dry with materialThe extracts are combined dried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-edf6976eea544bdbb6c173af585babb4
- Source dataset
- uspto-grants-2007_11
- Patent number
- US07297705B2
Reaction notes
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