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3-Phenoxybenzoic acid → N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-3-phenoxybenzamide

HRID 1777694
ノート
印刷プレビュー

反応式

HRID 1777694 の反応式
[O:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[Cl:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[C:22]2[CH2:28][CH2:29][NH2:30].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[C:22]2[CH2:28][CH2:29][NH:30][C:11](=[O:13])[C:10]1[CH:14]=[CH:15][CH:16]=[C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:9]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 195393-Phenoxybenzoic acidHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 67973697N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-3-phenoxybenzamide収率 19%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

A mixture of 3-phenoxybenzoic acid (0.200 g, 0.934 mmol), 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.215 g; 0.934 mmol), HATU (0.389 g; 1.03 mmol) and N,N-diisopropylethyldiamine (0.402 mL; 2.33 mmol) in DMF (5 mL), was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulphate, the organic layer was washed with sodium carbonate, brine, dried and concentrated in vacuo. The crude mixture was purified twice by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.068 g (19%) of the title compound as a colourless solid.

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulphate
  2. washthe organic layer was washed with sodium carbonate, brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe crude mixture was purified twice by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-076f60cca563439a82b415b9e098e971
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09266832B2

反応ノート

読み込み中…

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