Triacetoxyperiodinane → N-(4-Acetyl-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)-2,6-difluorobenzamide

HRID 1255141Notes

Reaction equation

HRID 1255141 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)=[C:10]([CH:12]([OH:14])[CH3:13])[N:11]=1)=[O:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:12]([C:10]1[N:11]=[C:7]([NH:6][C:4](=[O:5])[C:3]2[C:25]([F:29])=[CH:26][CH:27]=[CH:28][C:2]=2[F:1])[S:8][C:9]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:22])([F:23])[F:24])[CH:16]=1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 590045552,6-Difluoro-N-(4-(1-hydroxyethyl)-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)benzamide

Product 1

HCID 24765682N-(4-Acetyl-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)-2,6-difluorobenzamideYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of Compound 74 (22 mg, 0.05 mmol) in CH2Cl2 (2 mL) was added Dess-Martin periodinate (22 mg, 0.05 mmol). The reaction mixture was stirred at room temperature for 30 minutes. The solvent was removed and the residue was purified by column chromatography on silica gel (eluted with 10-70% ethyl acetate in hexanes) gave Compound 84 (17.5 mg, 82%) as a white solid.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by column chromatography on silica gel (eluted with 10-70% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e9cb9c0dcdee4dd0965b25882838c996
Source dataset
uspto-grants-2013_06
Patent number
US08455658B2

Reaction notes

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