Water → 1-(6-Chloro-5-fluoroindol-1-yl)-2-ethylamine

HRID 392094ノート

反応式

HRID 392094 の反応式
[OH-].[Na+].[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][C:5]=1[F:13].Cl.Cl[CH2:16][CH2:17][NH2:18].O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[Cl:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH2:16][CH2:17][NH2:18])=[CH:6][C:5]=1[F:13]

参加物

7

反応物 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 27736486-Chloro-5-fluoro-1H-indoleHCID 97937372-Chloroethylamine hydrochloride

生成物 1

HCID 189862171-(6-Chloro-5-fluoroindol-1-yl)-2-ethylamine収率 80%

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 6342Acetonitrile溶媒

実験手順

Tetra-n-butylammonium hydrogensulfate (0.1 g, 0.33 mmol), powdered sodium hydroxide (1.3 g, 33 mmol) and 6-chloro-5-fluoroindole (1.4 g, 8.3 mmol) were stirred at room tempera in acetonitrile (40 mL) for 1 h. 2-Chloroethylamine hydrochloride (1.45 g, 12.5 mmol) was then added in 1 portion and the reaction was heated to reflux and stirred for 36 h. After allowing to cool to room temperature the mixture was poured into water (100 mL) and extracted with ethyl acetate (3×70 mL). The combined organic extracts were washed with brine (1×100 mL), dried (magnesium sulfate), filtered and the solvent removed under vacuo to leave a crude oil. The oil was purified by flash column chromatography [SiO2; ethyl acetate-methanol-ammonium hydroxide, (90:9:1)] to give the product as an orange oil (1.4 g, 80%). IR νmax (film)/cm−1 3377, 3104, 2937, 2868, 1675, 1568, 1505, 1479, 1449, 1400, 1357, 1327, 1291, 1236, 1143, 1090, 1030, 994, 862, 817, 753, 717, 698, 678, 646, 633, 596 and 579; NMR δH (400 MHz; DMSO-d6) 7.79 (1H, d, J 7 Hz), 7.51 (1H, d, J 10 Hz), 7.50 (1H, d, J 3.5 Hz), 6.46 (1H, m), 4.13 (2H, t, J 6.3 Hz), 2.86 (2H, t, J 6.3 Hz), 1.52 (1H, br. s).

後処理

  1. temperaturethe reaction was heated
  2. temperatureto reflux
  3. extractionextracted with ethyl acetate (3×70 mL)
  4. washThe combined organic extracts were washed with brine (1×100 mL)
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. customthe solvent removed under vacuo
  8. customto leave a crude oil
  9. customThe oil was purified by flash column chromatography [SiO2; ethyl acetate-methanol-ammonium hydroxide, (90:9:1)]

出典と根拠

ORDレコード
ord-ee3dffba2e4e4d8a9be055add0babc5f
出典データセット
uspto-grants-2004_10
特許番号
US06800627B1

反応ノート

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