Benzoyl chloride → HCID 131724857、化合物

HRID 605885ノート

反応式

HRID 605885 の反応式
[C:1](Cl)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NC1[C:12](Cl)=[N:13][C:14]([Cl:17])=[CH:15][CH:16]=1.C(=O)([O-])[O-:20].[Na+].[Na+].C[C:26]([N:28](C)C)=O>C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:17][C:14]1[NH:13][C:12](=[O:20])[C:1]2[C:16]([CH:15]=1)=[N:28][CH:26]=[C:7]1[C:2]=2[CH:3]=[CH:4][CH:5]=[CH:6]1

参加物

7

反応物 4

HCID 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 1128462,6-Dichloro-3-pyridylamine

生成物 1

HCID 131724857HCID 131724857、化合物収率 13%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6344Dichloromethane溶媒

反応条件

温度
125 °C

実験手順

Amide 5 was prepared from commercial reagents, benzoyl chloride and 3-amino-2,6-dichloropyridine in DCM in high yield. The desired product 4g was prepared by dissolving amide 5 (4.45 g, 16.7 mmol) in DMA (35 mL) and adding sodium carbonate (1.8 g, 16.7 mmol) and palladium acetate (400 mg, catalytic amt.). The reaction mixture was heated to 125° C. for several hours until the stating material was no longer present by TLC. The reaction was then cooled down to room temperature and concentrated in vacuo and the crude residue was suspended in boiling EtOAc (100 mL) and filtered through a plug of celite. The filtrate was concentrated and the solid that precipitated out was filtered off and determined to be compound 4g (520 mg, 13% yield). Mp=285-295 (dec.) ° C.; 1H NMR (d6-DMSO) δ 11.92 (bs, 1H), 8.62 (d, 1H), 8.32 (d, 1H), 7.95 (t, 1H), 7.77 (m, 2H), 7.62 (d, 1H). Anal Calcd. for C12H7ClN2O: C, 62.49; H, 3.06; N, 12.15. Found: C, 61.40; H, 3.19; N, 11.77.

後処理

  1. customThe desired product 4g was prepared
  2. temperatureThe reaction was then cooled down to room temperature
  3. concentrationconcentrated in vacuo
  4. filtrationfiltered through a plug of celite
  5. concentrationThe filtrate was concentrated
  6. customthe solid that precipitated out
  7. filtrationwas filtered off

出典と根拠

ORDレコード
ord-c1c0117d5a3647f49a6c4ec290315969
出典データセット
uspto-grants-2011_03
特許番号
US07915280B2

反応ノート

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