Sodium Carbonate → 2,2-Dimethyl-n-(6-thiomorpholin-4-yl-4-o-tolyl-pyridin-3-yl)-propionamide

HRID 22644노트

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HRID 22644 반응식
I[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][S:11][CH2:10][CH2:9]2)[N:5]=[CH:4][C:3]=1[NH:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17].C(=O)([O-])[O-].[Na+].[Na+].[C:27]1([CH3:36])[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=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.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH3:17][C:16]([CH3:19])([CH3:18])[C:15]([NH:14][C:3]1[CH:4]=[N:5][C:6]([N:8]2[CH2:13][CH2:12][S:11][CH2:10][CH2:9]2)=[CH:7][C:2]=1[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH3:36])=[O:20]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 22591449n-(4-Iodo-6-thiomorpholin-4-yl-pyridin-3-yl)-2,2-dimethyl-propionamide

생성물 1

HCID 225914462,2-Dimethyl-n-(6-thiomorpholin-4-yl-4-o-tolyl-pyridin-3-yl)-propionamide

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

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온도
80 °C

실험 절차

A mixture of 4.05 g (10.0 mmol) N-(4-iodo-6-thiomorpholin-4-yl-pyridin-3-yl)-2,2-dimethyl-propionamide, 54 ml toluene, 16 ml 2 N sodium carbonate solution, 347 mg (0.3 mmol) tetrakis(triphenylphosphine)palladium(0), 67 mg (0.3 mmol) palladium(II) acetate and 1.50 g (11.0 mmol) o-tolylboronic acid was heated under argon at 80° C. for 18 h. After cooling to room temperature, the aqueous phase was separated and washed twice with ethyl acetate. The combined organic layers were washed with 50 ml brine, dried (sodium sulfate) and evaporated. Purification by flash-chromatography gave 3.57 g (quantitative) of the title compound as a light brown solid.

후처리

  1. temperatureAfter cooling to room temperature
  2. customthe aqueous phase was separated
  3. washwashed twice with ethyl acetate
  4. washThe combined organic layers were washed with 50 ml brine
  5. dry with materialdried (sodium sulfate)
  6. customevaporated
  7. customPurification by flash-chromatography

출처 및 근거

ORD 기록
ord-cc3b350c60d249e1a0c9ddbd7e0f52b9
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849624B2

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