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

HRID 595659ノート

反応式

HRID 595659 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 70681Tetrabutylammonium Chloride触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e11f2d32e876405abfbec2a0288975c8
出典データセット
uspto-grants-2016_01
特許番号
US09243002B2

反応ノート

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