Chlorosuccinimide → 3-chloro-1H-indole-4-carbonitrile

HRID 475169ノート

反応式

HRID 475169 の反応式
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]#[N:11])[C:4]=2[CH:3]=[CH:2]1.C1C(=O)N([Cl:19])C(=O)C1>CN(C=O)C.CCOC(C)=O>[Cl:19][C:3]1[C:4]2[C:5]([C:10]#[N:11])=[CH:6][CH:7]=[CH:8][C:9]=2[NH:1][CH:2]=1

参加物

5

反応物 2

HCID 31398ChlorosuccinimideHCID 38176024-Cyanoindole

生成物 1

HCID 866947173-chloro-1H-indole-4-carbonitrile収率 98.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To 1H-indole-4-carbonitrile (514.0 mg, 3.61 mmol) in anhydrous DMF (2.8 mL) at 0° C. was added dropwise NCS (517.3 mg, 3.80 mmol) dissolved in DMF (8.5 mL). The reaction mixture was slowly warmed to RT. After stirring for 20 h, the mixture was diluted with EtOAc. The organic layer was washed with satd. aq. NaHCO3 solution, water and brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by SiO2 chromatography eluting with heptane:EtOAc to afford 3-chloro-1H-indole-4-carbonitrile as a white solid (630 mg, 98.7%). MS (ESI) m/z: 177.1 [M+1]+. 1H NMR (400 MHz, DMSO) 11.99 (br s, 1H), 7.80 (d, J=2.8 Hz, 1H), 7.78 (d, J=8.2 Hz, 1H), 7.61 (d, J=7.2 Hz, 1H), 7.37-7.26 (m, 1H).

後処理

  1. washThe organic layer was washed with satd
  2. dry with materialaq. NaHCO3 solution, water and brine, dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by SiO2 chromatography
  6. washeluting with heptane

出典と根拠

ORDレコード
ord-73686851b2e746c7b6caa89d50517e00
出典データセット
uspto-grants-2014_01
特許番号
US08637537B2

反応ノート

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