Triethylamine → N-(5-bromo-2-chloropyridin-3-yl)-2-nitrobenzamide

HRID 44243

反応式

HRID 44243 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([Cl:8])=[N:6][CH:7]=1.C(N(CC)CC)C.[N+:17]([C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](Cl)=[O:23])([O-:19])=[O:18]>O1CCCC1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:22](=[O:23])[C:21]2[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=2[N+:17]([O-:19])=[O:18])[C:5]([Cl:8])=[N:6][CH:7]=1

参加物

7

反応物 3

HCID 8471TriethylamineHCID 118752-Nitrobenzoyl chlorideHCID 218583543-Amino-5-bromo-2-chloropyridine

生成物 1

HCID 86658034N-(5-bromo-2-chloropyridin-3-yl)-2-nitrobenzamide

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of 5-bromo-2-chloropyridine-3-amine (3.9 g, 18.9 mmol) and triethylamine (5.3 mL, 37.9 mmol) in tetrahydrofuran (60 mL) was added 2-nitrobenzoylchloride (2.49 mL, 18.9 mmol). The reaction was stirred for 24 hours. The reaction mixture was diluted with ethyl acetate (200 mL) and saturated aqueous sodium bicarbonate (60 mL). The organic layer was separated and washed with water (50 mL), brine (50 mL), dried over sodium sulfate, filtered and concentrated to dryness under reduced pressure. The crude product was purified by flash chromatography (SiO2, 25% ethyl acetate in hexanes). The N-(5-bromo-2-chloropyridin-3-yl)-2-nitrobenzamide was obtained as a yellow solid (1.5 g). LCMS [M+H]: 356.

後処理

  1. customThe organic layer was separated
  2. washwashed with water (50 mL), brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe crude product was purified by flash chromatography (SiO2, 25% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-ab89fc2dc2b24ffea8f46cdcfcbc29fa
出典データセット
uspto-grants-2013_09
特許番号
US08541407B2

関連ノート

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