Reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][N:10](CC3C=CC(OC)=CC=3)[C:6]=2[C:5]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:4][N:3]=1.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(O)(C(F)(F)F)=O.C1(OC)C=CC=CC=1.S(=O)(=O)(O)O>[Cl:1][C:2]1[C:7]2[CH:8]=[CH:9][NH:10][C:6]=2[C:5]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:4][N:3]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
A solution of ethyl 4-chloro-1-{[4-(methyloxy)phenyl]methyl}-1H-pyrrolo[3,2-c]pyridine-7-carboxylate (1.00 g) in TFA (5 ml) and anisole (0.92 ml) was stirred at room temperature for 2.5 h. Sulphuric acid (5 drops) was added to the reaction mixture and stirring continued for 2 h then sulphuric acid (2 ml) was added and the reaction mixture stirred for 24 h at room temperature. The solution was added to saturated sodium bicarbonate at 0° C. and extracted with ethyl acetate. The aqueous layer was separated and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated to afford the title compound as a brown solid (0.50 g).
Workup
- stirringthe reaction mixture stirred for 24 h at room temperature
- extractionextracted with ethyl acetate
- customThe aqueous layer was separated
- extractionextracted three times with ethyl acetate
- washThe combined organic layers were washed with brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-5c6b7da5433c4a8c8cc6d86145654fa3
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589206B2
Linked notes
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