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

HRID 252192
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HRID 252192 반응식
[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
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참가 물질

10

반응물 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

생성물 1

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

시약·촉매·용매 5

HCID 83717
Copper iodide
촉매
HCID 176Acetic Acid용매
HCID 962Water용매
HCID 1140Toluene용매
HCID 8857Ethyl Acetate용매

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온도
110 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f53d76a0370940489ad956c4b9377b92
출처 데이터셋
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07868024B2

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