DMF Phosphorus oxychloride → 5-(difluoromethoxy)-1H-indole-3-carboxylic acid

HRID 57313Notes

Reaction equation

HRID 57313 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

Reactant 3

HCID 13765457DMF Phosphorus oxychlorideHCID 667379585-(difluoromethoxy)-1H-indoleHCID 86629097Sodium chlorite sodium dihydrogen phosphate

Product 1

HCID 576465145-(difluoromethoxy)-1H-indole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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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