Sodium periodate → 2,2,2-Trifluoro-N-(2-formylphenyl)acetamide

HRID 1796696Notes

Reaction equation

HRID 1796696 reaction equation
C(OC(C1O[C:8]2[C:13](C(=O)C=1)=[CH:12][CH:11]=[C:10]([NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[C:9]=2[CH:24]=CC)=O)C.I([O-])(=O)(=O)=[O:28].[Na+]>[Os](=O)(=O)(=O)=O>[F:22][C:19]([F:20])([F:21])[C:18]([NH:17][C:10]1[CH:11]=[CH:12][CH:13]=[CH:8][C:9]=1[CH:24]=[O:28])=[O:23]

Participants

4

Reactant 2

HCID 23667635Sodium periodateHCID 73710678HCID 73710678, compound

Product 1

HCID 145814612,2,2-Trifluoro-N-(2-formylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

Compounds of the invention in which R1 is alkyl may be prepared from the 8-propenyl-7-trifluoroacetamido-4-oxo-4H-chromene-2-carboxylic acid ethyl ester described above in accordance with Scheme II. The rearranged olefin (5) is treated with osmium tetroxide and sodium periodate to give the o-trifluoroacetamidobenzaldehyde (8). Condensation with the appropriate triphenylphosphorylidene ketone under Wittig conditions gives the o-trifluoroacetamidostyryl ketone (9), which upon treatment with acid cyclizes to give the 5-oxa-1-aza-phenanthrene ring system of the title compounds (10). Reduction, re-aromatization and tosylation as above gives the 7,8-dihydro-6H-5-oxa-1-aza-phenanthren-6-methyltosylate. Replacement of the tosylate with the appropriately substituted azaheterocycle as above gives the title compounds of the invention. Substitution of trimethyl phosphonoacetate for the triphenylphosphorylidene ketone in the Wittig procedure above, followed by cyclization in acid gives the compounds of the invention in which R1 is hydroxy. Alkylation of this hydroxy derivative by a suitable alkyl halide or tosylate in the presence of base gives the compounds of the invention in which R1 is alkoxy. Treatment of the hydroxy derivative with an inorganic acid chloride such as phosphoryl chloride or bromide gives the compounds of the invention in which R1 is halo. Substitution of diethyl cyanomethylphosphonate for the triphenylphosphorylidene ketone in the Wittig procedure above, followed by cyclization in acid gives the compounds of the invention in which R1 is amino.

Sources & evidence

ORD record
ord-0091624552914f4ab6022f3e95c89b72
Source dataset
uspto-grants-2006_04
Patent number
US07030245B2

Reaction notes

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