DMF Phosphorus oxychloride → 5-(difluoromethoxy)-1H-indole-3-carboxylic acid
Reaction equation
[F:1][CH:2]([F:13])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.P(Cl)(Cl)(Cl)=O.CN([CH:22]=[O:23])C.Cl([O-])=[O:25].[Na+].P([O-])(O)(O)=O.[Na+]>O1CCOCC1>[F:13][CH:2]([F:1])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:22]([OH:23])=[O:25]Participants
5
Procedure
5-Difluoromethoxyindole (PCT 2007/096395) was formylated at the 3-position using the Vilsmeyer-Haack protocol (phosphorous oxychloride/DMF). The resulting aldehyde was oxidized with sodium chlorite/sodium dihydrogen phosphate in aqueous dioxane. MS (m/e) 227.
Sources & evidence
- ORD record
- ord-1003ecbd72b848fda0859a211150ff71
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434724B2
Reaction notes
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