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

HRID 22644

反応式

HRID 22644 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cc3b350c60d249e1a0c9ddbd7e0f52b9
出典データセット
uspto-grants-2005_02
特許番号
US06849624B2

関連ノート

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