Benzene, 1-bromo-4-(trifluoromethyl)- → HCID 136492447, compound

HRID 508936Notes

Reaction equation

HRID 508936 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[NH:13][C:12](=[O:14])[N:11]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([NH2:21])=[O:20])=[CH:17][CH:16]=2)[N:10]=1.Br[C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[NH:13][C:12](=[O:14])[N:11]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([NH:21][C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=3)=[O:20])=[CH:17][CH:16]=2)[N:10]=1

Participants

5

Reactant 3

HCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 23676156Sodium t-butoxideHCID 136492349HCID 136492349, compound

Product 1

HCID 136492447HCID 136492447, compoundYield 10.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-(3-(2-chloro-6-fluorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)benzamide (Intermediate-17, 0.100 g, 0.301 mmol) in dry toluene (5 mL) was added 1-bromo-4-(trifluoromethyl)benzene (0.101 g, 0.451 mmol), sodium tert-butoxide (0.058 g, 0.602 mmol), tris(diphynylideneacetone)dipalladium(0) (0.005 g, 0.0006 mmol), 4,5 bis(diphenylphosphino) and 9,9-dimethylxanthene (0.005 g, 0.0009 mmol) under nitrogen atmosphere. The reaction mass was refluxed for 3-4 h. The reaction mass was quenched in water and extracted in ethyl acetate. The organic layer was concentrated to afford crude product which was purified by column chromatography to afford 0.015 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 7.40 (br s, 1H), 7.84 (t, J=9 Hz, 1H), 7.55 (d, 1H), 7.72-7.75 (m, 3H), 8.02 (d, J=8.1 Hz, 2H), 8.11 (br s, 3H) 10.61 (br s, 1H), 12.70 (br s, 1H). MS (m/z): 475.18 (M−H)−.

Workup

  1. temperatureThe reaction mass was refluxed for 3-4 h
  2. customThe reaction mass was quenched in water
  3. extractionextracted in ethyl acetate
  4. concentrationThe organic layer was concentrated
  5. customto afford crude product which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-1582531b324c4bb78f3cbcaf61d658b9
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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