Pyridine → HCID 71257495、化合物

HRID 710091ノート

反応式

HRID 710091 の反応式
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.N1C=CC=CC=1.[F:16][C:17]1[CH:25]=[C:24]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:23]=[CH:22][C:18]=1[C:19](Cl)=[O:20]>C(Cl)Cl.O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:19](=[O:20])[C:18]2[CH:22]=[CH:23][C:24]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:25][C:17]=2[F:16])=[C:4]([F:9])[CH:3]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 1230504-Bromo-2-fluoroanilineHCID 189779422-Fluoro-4-(methylsulfonyl)benzoyl chloride

生成物 1

HCID 71257495HCID 71257495、化合物収率 34.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

2-Fluoro-4-(methylsulfonyl)benzoic acid (2 g, 9.2 mmol) dissolved in DCM (10 ml), cooled to 0° C. and added oxalyl chloride (1.2 ml, 13.8 mmol). Catalytic amount of DMF was added to this mixture and stirred at rt for 30 mins. After 30 mins, DCM removed on rotavapour and co-distilled the residue two times with DCM to obtain 2-fluoro-4-(methylsulfonyl)benzoyl chloride quantitatively. 4-Bromo-2-fluoroaniline (1.4 g, 7.37 mmol) dissolved in DCM and added Pyridine (0.7 g, 8.84 mmol) under nitrogen atmosphere. This mixture stirred at rt for 30 mins and added 2-fluoro-4-(methylsulfonyl)benzoyl chloride (2.08 g, 8.84 mmol). After continuing stifling at rt for 15 mins, reaction mixture diluted with water and extracted with DCM. DCM layer washed with aq. NaHCO3 and DCM removed on rotavapour to obtain the solid. Solid was triturated with Et2O and Petether mixture (4:1) to obtain the titled compound (1 g) as a brown solid.

後処理

  1. waitAfter continuing stifling at rt for 15 mins
  2. customreaction mixture
  3. extractionextracted with DCM
  4. washDCM layer washed with aq. NaHCO3 and DCM
  5. customremoved on rotavapour
  6. customto obtain the solid
  7. customSolid was triturated with Et2O and Petether mixture (4:1)

出典と根拠

ORDレコード
ord-0652c70c631a48669e33f6a0389fdd74
出典データセット
uspto-grants-2015_11
特許番号
US09181214B2

反応ノート

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