5-Methoxyindole → 2-(5-methoxy-1H-indol-3-yl)-2-oxoacetyl chloride
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[C:12](Cl)(=[O:16])[C:13]([Cl:15])=[O:14]>C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:12](=[O:16])[C:13]([Cl:15])=[O:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 5-methoxyindole (10.00 g, 67.95 mmol) in diethylether (200 mL), oxalyl chloride (7.79 mL, 88.33 mmol) was added at 0° C. After stirring at rt for 3 h, the solid was filtered off and washed with cold diethylether to yield 2-(5-methoxy-1H-indol-3-yl)-2-oxoacetyl chloride as a orange solid which was used as such in the next step. LC-MS conditions B: tR=0.46 min, no ionization.
Workup
- filtrationthe solid was filtered off
- washwashed with cold diethylether
Sources & evidence
- ORD record
- ord-7442a7aa742a4c8ea716f31076bc81d9
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09303023B2
Reaction notes
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