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

HRID 578863Notes

Reaction equation

HRID 578863 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-b667011227f74d49b5cc51ffb6e1569a
Source dataset
uspto-grants-2015_05
Patent number
US09040708B2

Reaction notes

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