Water → N-[[1-(5-bromo-3-chloro-2-pyridyl)cyclopropyl]methyl]-2-(trifluoromethyl)benzamide

HRID 578863ノート

反応式

HRID 578863 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([Cl:13])[C:5]([C:8]2([CH2:11][NH2:12])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.C(N(CC)CC)C.[F:21][C:22]([F:33])([F:32])[C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26].O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([Cl:13])[C:5]([C:8]2([CH2:11][NH:12][C:25](=[O:26])[C:24]3[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=3[C:22]([F:21])([F:32])[F:33])[CH2:9][CH2:10]2)=[N:6][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 89544163(1-(5-Bromo-3-chloropyridin-2-yl)cyclopropyl)methanamine

生成物 1

HCID 89544470N-[[1-(5-bromo-3-chloro-2-pyridyl)cyclopropyl]methyl]-2-(trifluoromethyl)benzamide収率 95.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

3 g C-[1-(5-bromo-3-chloro-pyridin-2-yl)-cyclopropyl]-methylamine (step 3) was dissolved in 20 ml of dichloromethane and was cooled down to 0° C. 2.32 g of triethylamine was added, then a solution of 2.87 g 2-(trifluoromethyl)benzoyl chloride 5 ml dichloromethane was added dropwise. The reaction mixture was stirred at ambient temperature for 2 hours. Then water was added and the mixture was extracted twice with dichloromethane. The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated. Crude material was obtained as a pale yellow sticky solid, which was purified by flash chromatography on silica gel with heptane/ethyl acetate as a solvent. Thus, 4.74 g of N—[[1-(5-bromo-3-chloro-2-pyridyl)cyclopropyl]methyl]-2-(trifluoromethyl)benzamide was obtained as a colourless sticky solid. 1H-NMR (CDCl3): 8.45 ppm (s, 1H), 7.87 ppm (s, 1H), 7.65 ppm (d, 1H), 7.52 ppm (m, 2H), 7.41 ppm (d, 1H), 6.10 ppm (s, 1H, broad), 3.70 ppm (d, 2H), 1.10 ppm (m, 4H).

後処理

  1. extractionthe mixture was extracted twice with dichloromethane
  2. dry with materialThe organic phase was dried with anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customCrude material was obtained as a pale yellow sticky solid, which
  6. customwas purified by flash chromatography on silica gel with heptane/ethyl acetate as a solvent

出典と根拠

ORDレコード
ord-b667011227f74d49b5cc51ffb6e1569a
出典データセット
uspto-grants-2015_05
特許番号
US09040708B2

反応ノート

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