Triacetoxyperiodinane → 1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-formylphenyl)urea

HRID 1843047Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([CH2:13][NH:14][C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][OH:25])=[C:20]([F:26])[CH:19]=3)=[O:16])=[CH:11][C:10]([C:27]([F:30])([F:29])[F:28])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([CH2:13][NH:14][C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH:24]=[O:25])=[C:20]([F:26])[CH:19]=3)=[O:16])=[CH:11][C:10]([C:27]([F:30])([F:28])[F:29])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-(hydroxymethyl)phenyl)urea (240 mg, 0.54 mmol, 1.0 eq) in DCM (10 mL) and cooled to 0° C. was added Dess-Martin periodinane (345 mg, 0.813 mmol, 1.5 eq) slowly portion wise at 0° C. and stirred for 1 h at 0° C., and then stirred for 30 min. at RT. DCM was evaporated and EtOAC (50 mL) was added. The mixture was washed with water (20 mL), brine (20 mL), dried over anhydrous Na2SO4 and evaporated under vacuum. The crude product was purified by CC using EtOAc/PE (2:3) to yield compound 1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-formylphenyl)urea (120 mg; 48%) as an yellow solid (TLC: EtOAc/PE (1:1); Rf: 0.5).

Workup

stirringstirred for 30 min. at RT
customDCM was evaporated
additionEtOAC (50 mL) was added
washThe mixture was washed with water (20 mL), brine (20 mL)
dry with materialdried over anhydrous Na2SO4
customevaporated under vacuum
customThe crude product was purified by CC

Sources & evidence

ORD record: ord-e4f632db2b374d97aff3e85f7e26435a
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946204B2

Reaction notes

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