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

HRID 475169노트

반응식

HRID 475169 반응식
[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

참가 물질

5

반응물 2

HCID 31398ChlorosuccinimideHCID 38176024-Cyanoindole

생성물 1

HCID 866947173-chloro-1H-indole-4-carbonitrile수율 98.8%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-73686851b2e746c7b6caa89d50517e00
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637537B2

반응 노트

불러오는 중…