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

HRID 1843047ノート

反応式

HRID 1843047 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e4f632db2b374d97aff3e85f7e26435a
出典データセット
uspto-grants-2015_02
特許番号
US08946204B2

反応ノート

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