Potassium Hydroxide → 2-Chloro-10-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridine

HRID 595659노트

반응식

HRID 595659 반응식
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][C:13]([F:17])=[CH:12][CH:11]=3)[C:5]([CH:18]=[CH2:19])=[CH:4][CH:3]=1.[OH-].[K+]>CCCC[N+](CCCC)(CCCC)CCCC.[Cl-].CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:18][CH2:19][N:9]3[C:10]4[CH:11]=[CH:12][C:13]([F:17])=[CH:14][C:15]=4[CH:16]=[C:8]3[C:6]=2[N:7]=1

참가 물질

5

반응물 2

HCID 14797Potassium HydroxideHCID 903339502-(6-chloro-3-vinylpyridin-2-yl)-5-fluoro-1H-indole

생성물 1

HCID 903334282-Chloro-10-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridine수율 50.9%

시약·촉매·용매 2

HCID 70681Tetrabutylammonium Chloride촉매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
100 °C

실험 절차

A mixture of 2-(6-chloro-3-vinylpyridin-2-yl)-5-fluoro-1H-indole (100 mg, 0.36 mmol), DMSO (0.5 mL), TBAC (0.1 mL of 50% a.q. solution) and KOH (1.0 mL of 60% a.q. solution) was stirred under N2 at 100° C. for 4 h. After cooled and extracted with EtOAc, the organic layer was washed with water, brine, dried over Na2SO4, and concentrated. The residue was purified by prep-TLC (PE:EA=10:1) to give the product of 2-chloro-10-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridine (50 mg, yield: 50.0%). 1H-NMR (CDCl3, 400 MHz) δ 7.51 (d, J=8.0 Hz, 1H), 7.25˜7.38 (m, 3H), 7.15 (d, J=8.0 Hz, 1H), 6.98˜7.04 (m, 1H), 4.26 (d, J=6.4 Hz, 2H), 3.22 (d, J=6.4 Hz, 2H). MS (M+H)+: 273/275.

후처리

  1. temperatureAfter cooled
  2. extractionextracted with EtOAc
  3. washthe organic layer was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by prep-TLC (PE:EA=10:1)

출처 및 근거

ORD 기록
ord-e11f2d32e876405abfbec2a0288975c8
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09243002B2

반응 노트

불러오는 중…