Sodium Chlorite → 2-Chloro-5-methoxy-1-phenyl-1h-indole-3-carboxylic acid

HRID 1510080Notes

Reaction equation

[Cl:1][C:2]1[N:3]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][C:7]([O:13][CH3:14])=[CH:6][CH:5]=2.Cl([O-])=[O:22].[Na+].P([O-])(O)(O)=O.[Na+]>C(O)(C)(C)C.CC(=CC)C.O>[Cl:1][C:2]1[N:3]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:4]2[C:9]([C:10]=1[C:11]([OH:22])=[O:12])=[CH:8][C:7]([O:13][CH3:14])=[CH:6][CH:5]=2

Participants

Conditions

Temperature: 80 °C

Procedure

The compound of step 3 (456 mg, 1.59 mmol) was dissolved in tert-butanol (15 ml) and 2-methyl-2-butene (3 ml), and a solution of sodium chlorite (1.32 g, 14.6 mmol) and sodium dihydrogenphosphate (1.32 g, 11.0 mmol) in water (6 ml) was added. The reaction mixture was stirred at room temperature for 48 h and afterwards at 80° C. for 2.5 h. The mixture was diluted with water and extracted with EA. The organic layer was dried over sodium sulfate, filtered and the solvent was removed under reduced pressure to give 602 mg of the crude title compound.

Workup

extractionextracted with EA
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-353e6e89576140e1ba0c3e512d837320
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211885B2

Reaction notes

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