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Potassium Phosphate, Tribasic → Ethyl 5-fluoro-1-(4,6-dimethylpyridin-2-yl)-1H-indole-2-carboxylate

HRID 252192
ノート
印刷プレビュー

反応式

HRID 252192 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.Br[C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[N:18]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNC1CCCCC1NC>[Cu](I)I.C(OCC)(=O)C.C(O)(=O)C.O.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[N:18]=1)[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

10

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 2727899ethyl 5-fluoro-1H-indole-2-carboxylateHCID 149751952-Bromo-4,6-dimethylpyridine

生成物 1

HCID 66845370Ethyl 5-fluoro-1-(4,6-dimethylpyridin-2-yl)-1H-indole-2-carboxylate収率 84.8%

試薬・触媒・溶媒 5

HCID 83717
Copper iodide
触媒
HCID 176Acetic Acid溶媒
HCID 962Water溶媒
HCID 1140Toluene溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

4.35 g (21 mmol) of ethyl 5-fluoro-1H-indole-2-carboxylate, 4.29 g (23.1 mmol) of 2-bromo-4,6-dimethylpyridine, 9.36 g (44.1 mmol) of tripotassium phosphate, 0.66 ml (4.2 mmol) of 1,2-dimethylaminocyclohexane, 0.2 g (1.05 mmol) of copper iodide and 21 ml of dry toluene are added to a pressure tube. The tube is closed and the reaction mixture is stirred at 110° C. for 5 days. After this time, the mixture is poured onto a solution of 100 ml of water and the pH of the medium is adjusted to pH 5 by additions of acetic acid. 100 ml of ethyl acetate are added. The organic phase is separated, washed successively with 50 ml of water and 50 ml of a saturated aqueous sodium chloride solution, then dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue is purified by preparative chromatography (eluent: dichloromethane/ethyl acetate). 5.56 g of expected product are obtained, which product is used as is in the continuation of the synthesis.

後処理

  1. customThe tube is closed
  2. customThe organic phase is separated
  3. washwashed successively with 50 ml of water and 50 ml of a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by preparative chromatography (eluent: dichloromethane/ethyl acetate)

出典と根拠

ORDレコード
ord-f53d76a0370940489ad956c4b9377b92
出典データセット
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07868024B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート