Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[C:18]3[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16][NH:15][C:14](=O)[C:13]=3[CH:12]=[CH:11]2)=[CH:5][CH:4]=1.P(Cl)([Cl:34])(OC1C=CC=CC=1)=O.O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[Cl:34][C:14]1[C:13]2[CH:12]=[CH:11][N:10]([CH2:9][C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:18]=2[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16][N:15]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Ethyl 1-{[4-(methyloxy)phenyl]methyl}-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate (2.90 g) and phenyl dichlorophosphate (18 ml) were heated at 180° C. under argon for 30 minutes. The reaction mixture was allowed to cool, poured onto iced water, and neutralised to pH7 using solid sodium bicarbonate. To the reaction mixture was added ethyl acetate and the insoluble material was filtered off. The aqueous 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 clear oil (2.0 g).
Workup
- temperatureto cool
- filtrationthe insoluble material was filtered off
- customThe aqueous 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-73ad1c02fc9a4848ad7456417a31f865
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589206B2
Linked notes
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