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

HRID 1843047노트

반응식

HRID 1843047 반응식
[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

참가 물질

4

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 708160761-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-(hydroxymethyl)phenyl)urea

생성물 1

HCID 715731471-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-formylphenyl)urea수율 50.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-e4f632db2b374d97aff3e85f7e26435a
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946204B2

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