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Potassium Iodide → HCID 11998147, 화합물

HRID 2102693
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HRID 2102693 반응식
C(OC([CH:8]1[CH2:13][CH2:12][C:11]([CH:14]2[C:22]3[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:24])=[CH:10][NH:9]1)=O)(C)(C)C.Br[CH2:26][C:27]1[CH:32]=[C:31]([Cl:33])[N:30]=[C:29]([Cl:34])[CH:28]=1.[I-].[K+].[C:37](=[O:40])([O-])[O-:38].[K+].[K+]>CC(C)=O.C(OCC)(=O)C>[C:11]([O:38][C:37]([N:9]1[CH:10]=[C:11]([C:14]2([CH2:26][C:27]3[CH:32]=[C:31]([Cl:33])[N:30]=[C:29]([Cl:34])[CH:28]=3)[C:22]3[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:24])[CH2:12][CH2:13][CH2:8]1)=[O:40])([CH3:14])([CH3:12])[CH3:10]
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참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27818294-(Bromomethyl)-2,6-dichloropyridineHCID 68858815HCID 68858815, 화합물

생성물 1

HCID 11998147HCID 11998147, 화합물

시약·촉매·용매 2

HCID 180Acetone용매
HCID 8857
Ethyl Acetate
용매

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온도
60 °C

실험 절차

A mixture of 5-[6-chloro-2-oxo-2,3-dihydro-1H-indol-3-yl]-3,4-dihydro-2H-pyridine-carboxylic acid tert-butyl ester (0.32 g, 0.9 mmol) (from Example 20a supra), 4-bromomethyl-2,6-dichloro-pyridine (0.26 g, 1.08 mmol) (Maybridge), potassium iodide (0.18 g, 1.08 mmol) and potassium carbonate (0.27 g, 1.97 mmol) in acetone (30 mL) was heated at 60° C. for 2 hours in a capped pressure tube. After cooling, mixture was diluted with ethyl acetate and washed with water and brine. Aqueous layers were back washed with ethyl acetate. The organic layers were combined, dried over Na2SO4 and concentrated. The residue was purified by chromatography (ethyl acetate-dichloromethane, 25:75, V/V) to give rac-5-[6-chloro-3-(2,6-dichloro-pyridin-4-ylmethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-3,4-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester as a white solid. (Yield 0.28 g, 60%).

후처리

  1. temperatureAfter cooling
  2. washwashed with water and brine
  3. washAqueous layers were back washed with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (ethyl acetate-dichloromethane, 25:75, V/V)

출처 및 근거

ORD 기록
ord-84fddb62e1944b04aa167c9362bded90
출처 데이터셋
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07576082B2

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