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Sodium Carbonate → N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-2,2-dimethyl-propionamide

HRID 1017439
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인쇄 미리보기

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HRID 1017439 반응식
[CH3:1][CH:2]([CH3:13])[C:3]([NH:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1I)=[O:4].[C:14](=O)([O-])[O-].[Na+].[Na+].[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:11]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[NH:5][C:3](=[O:4])[C:2]([CH3:13])([CH3:14])[CH3:1]
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참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 184033342,2-Dimethyl-n-(4-iodo-pyridin-3-yl)-acetamide

생성물 1

HCID 18403361N-[4-(2-Chloro-phenyl)-pyridin-3-yl]-2,2-dimethyl-propionamide수율 65%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매
HCID 1140
Toluene
용매

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온도
80 °C

실험 절차

A mixture of 35 g (115 mmol) 2,2-dimethyl-N-(4-iodo-pyridin-3-yl)-acetamide, 400 ml toluene, 120 ml 2 N sodium carbonate solution, 4.0 g (3.5 mmol) tetrakis(triphenylphosphine)palladium(0) and 20.0 g (128 mmol) o-chlorophenylboronic acid was heated under argon at 80° C. for 12 h. After cooling to room temperature, the aqueous phase was separated and washed twice with toluene. The combined organic layers were washed with 50 ml brine, dried (magnesium sulfate) and evaporated. The residue was purified by flash chromatography to yield 21.6 g (65%) of the title compound as white crystals.

후처리

  1. temperatureAfter cooling to room temperature
  2. customthe aqueous phase was separated
  3. washwashed twice with toluene
  4. washThe combined organic layers were washed with 50 ml brine
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated
  7. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-d38bb9d086ba4ffe96645ee3790ba0f1
출처 데이터셋
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06479483B2

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