Dichloromethane → N-(4-cyanomethyl-2-methoxy-phenyl)-3-trifluoromethyl-benzamide

HRID 1818926

反応式

HRID 1818926 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.ClCCl.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[O:24].CCN(C(C)C)C(C)C>CCOC(C)=O.[Pd].O>[C:13]([CH2:12][C:5]1[CH:6]=[CH:7][C:8]([NH:9][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][CH:28]=[C:20]([C:19]([F:18])([F:29])[F:30])[CH:21]=2)=[C:3]([O:2][CH3:1])[CH:4]=1)#[N:14]

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 81531DiisopropylethylamineHCID 136293172-(3-Methoxy-4-nitrophenyl)acetonitrile

生成物 1

HCID 68423610N-(4-cyanomethyl-2-methoxy-phenyl)-3-trifluoromethyl-benzamide

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Compound 19.2 (0.096 mmol), and catalytic Pd/C in EtOAc (2 mL) were placed under an atmosphere of hydrogen for 3 hours. The reaction mixture was filtered, concentrated and taken on crude to the next reaction. The crude compound (0.096 mmol), dichloromethane (0.5 mL), 3-(trifluoromethyl)benzoyl chloride (1.05 mmol) and DIEA (1.10 mmol) was stirred at room temperature for 10 minutes. Water was added after which the mixture partitioned between EtOAc and water. The organic layer was separated, washed with brine, dried, filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica gel using a gradient of EtOAc/hexanes provided N-(4-cyanomethyl-2-methoxy-phenyl)-3-trifluoromethyl-benzamide (compound 19.3) in 71%.

後処理

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customtaken on crude to the next reaction
  4. custompartitioned between EtOAc and water
  5. customThe organic layer was separated
  6. washwashed with brine
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customPurification by flash column chromatography on silica gel using a gradient of EtOAc/hexanes

出典と根拠

ORDレコード
ord-bf343513767548eaae3297953a3d71f5
出典データセット
uspto-grants-2009_10
特許番号
US07601725B2

関連ノート

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