Potassium Carbonate → HCID 68556375、化合物

HRID 2382104ノート

反応式

HRID 2382104 の反応式
[C:1]([O:5][C:6](=[O:18])[N:7]([CH2:15][CH:16]=[CH2:17])[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1Cl)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:7]1[C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[C:16]([CH3:17])=[CH:15]1)=[O:18])([CH3:4])([CH3:3])[CH3:2].[C:1]([O:5][C:6]([N:7]1[C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[C:16](=[CH2:17])[CH2:15]1)=[O:18])([CH3:4])([CH3:3])[CH3:2]

参加物

8

反応物 2

HCID 11430Potassium CarbonateHCID 68557669Carbamic acid, N-(3-chloro-4-pyridinyl)-N-2-propen-1-yl-, 1,1-dimethylethyl ester

生成物 2

HCID 68555346HCID 68555346、化合物HCID 68556375HCID 68556375、化合物収率 117.7%

試薬・触媒・溶媒 4

HCID 70681Tetrabutylammonium Chloride触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of allyl-(3-chloro-pyridin-4-yl)-carbamic acid tert-butyl ester (8.25 g, 30.8 mmol), tetrabutylammonium chloride (9.67 g, 30.8 mmol), palladium acetate (691 mg, 3.08 mmol) and potassium carbonate (12.8 g, 92.3 mmol) in DMF (100 mL) is heated at 800 C. for 1.5 h. The reaction is diluted with DCM and washed three times with water. The organic layer is dried (Na2SO4), filtered and concentrated. The residue is chromatographed through silica gel eluting with 0-40% EtOAc in heptane to afford a mixture 3-methyl-pyrrolo [3,2-c]pyridine-1-carboxylic acid tert-butyl ester and 3-methylene-2,3-dihydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (4.21 g, total).

後処理

  1. temperatureis heated at 800 C
  2. washwashed three times with water
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is chromatographed through silica gel eluting with 0-40% EtOAc in heptane

出典と根拠

ORDレコード
ord-3bd95e96910e4a518c80c917ada22c09
出典データセット
uspto-grants-2012_09
特許番号
US08258130B2

反応ノート

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