Triethyl phosphite → ethyl 2-(5-methyl-2H-indazol-2-yl)benzoate

HRID 274130Notes

Reaction equation

P(OCC)(OCC)OCC.[CH3:11][C:12]1[CH:13]=[CH:14][C:15]([N+:31]([O-])=O)=[C:16]([CH:30]=1)[CH:17]=[N:18][C:19]1[C:20](=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22]>>[CH3:11][C:12]1[CH:13]=[CH:14][C:15]2[C:16](=[CH:17][N:18]([C:19]3[CH:29]=[CH:28][CH:27]=[CH:26][C:20]=3[C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:31]=2)[CH:30]=1

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 20094566HCID 20094566, compound

Product 1

HCID 20094524ethyl 2-(5-methyl-2H-indazol-2-yl)benzoateYield 64.3%

Procedure

Triethyl phosphite (5.8 ml, 34 mmol) was added to ethyl N-(5-methyl-2-nitrobenzylidene)anthranilate (3.10 g, 9.93 mmol) as obtained in Reference Example 2. The mixture was refluxed under heating for 4 hours, and the triethyl phosphite was evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel using a mixed solvent of hexane/ethyl acetate (5:1), whereby 1.79 g of ethyl 2-(5-methyl-2H-indazol-2-yl)benzoate was obtained.

Workup

customas obtained in Reference Example 2
temperatureThe mixture was refluxed
temperatureunder heating for 4 hours
customthe triethyl phosphite was evaporated under reduced pressure
customThe residue was purified by flash chromatography on silica gel using a mixed solvent of hexane/ethyl acetate (5:1)

Sources & evidence

ORD record: ord-658b2354aa6f432f91303ec0e087e465
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05387684

Reaction notes

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