Phosphorus oxychloride → N-(5-bromo-2-pyridinyl)-(2-nitro)-5fluorophenylcarboxamide

HRID 12138

反応式

HRID 12138 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][N:16]=1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:7]([C:6]2[CH:10]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[N+:11]([O-:13])=[O:12])=[O:9])=[N:16][CH:17]=1

参加物

5

反応物 3

HCID 24813Phosphorus oxychlorideHCID 706222-Amino-5-bromopyridineHCID 27374205-Fluoro-2-nitrobenzoic acid

生成物 1

HCID 22596298N-(5-bromo-2-pyridinyl)-(2-nitro)-5fluorophenylcarboxamide収率 68.1%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A solution of 5-fluoro-2-nitrobenzoic acid (10.0 g, 54 mmol, 1.0 equiv), 2-amino-5-bromopyridine (12.2 g, 1.3 equiv), in 80 mL of pyridine was treated with phosphorous oxychloride (25.3 g, 3.0 equiv) for 30 min. The volatile was evaporated and the residue was redissolved into EtOAc, washed with 1N HCl, saturated aqueous NaHCO3 and saturated aqueous NaCl. The organic layer was dried over Na2SO4, filtered, and evaporated. The volatile was evaporated, and the product was triturated with diethyl ether to give N-(5-bromo-2-pyridinyl)-(2-nitro)-5-fluorophenylcarboxamide (12.5 g, 68%). MS found for C12H7BrFN3O3 (M+H)+: 340, 342.

後処理

  1. customThe volatile was evaporated
  2. dissolutionthe residue was redissolved into EtOAc
  3. washwashed with 1N HCl, saturated aqueous NaHCO3 and saturated aqueous NaCl
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe volatile was evaporated
  8. customthe product was triturated with diethyl ether

出典と根拠

ORDレコード
ord-b7fdc228ba5a4a11b5ad77c59bddf049
出典データセット
uspto-grants-2010_06
特許番号
US07727982B2

関連ノート

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