Pyridinium, 1-fluoro-, 1,1,1-trifluoromethanesulfonate (1:1) → 3-fluoro-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

HRID 1188450ノート

反応式

HRID 1188450 の反応式
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[C:8]([C:11]([F:14])([F:13])[F:12])[C:7]([C:15]#[N:16])=[CH:6][CH:5]=2.[O-]S(C(F)(F)[F:22])(=O)=O.F[N+]1C=CC=CC=1>C(Cl)Cl>[F:22][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:15]#[N:16])[C:8]=2[C:11]([F:12])([F:14])[F:13])[NH:3][C:2]=1[CH3:1]

参加物

4

反応物 2

HCID 2724576Pyridinium, 1-fluoro-, 1,1,1-trifluoromethanesulfonate (1:1)HCID 533093462-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

生成物 1

HCID 578003103-fluoro-2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile収率 22.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile (0.063 g, 0.28 mmol) in CH2Cl2 (4 mL) was added 1-fluoropyridinium triflate (0.104 g, 0.42 mmol) and stirred at rt for 3 days. The mixture was partitioned between EtOAc and 0.1N HCl. The organic phase was washed with 0.1N HCl and sat'd brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by flash chromatography (10-50% EtOAc-hexanes gradient) to afford the title compound as a white solid (0.015 g, 22% yield, 94% purity): MS (ES) m/z 243 (M+1).

後処理

  1. customThe mixture was partitioned between EtOAc and 0.1N HCl
  2. washThe organic phase was washed with 0.1N HCl
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (10-50% EtOAc-hexanes gradient)

出典と根拠

ORDレコード
ord-0428760fb9784870bab30b573c2046ec
出典データセット
uspto-grants-2014_03
特許番号
US08673948B2

反応ノート

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