Cesium carbonate → 3-bromo-7-(2-chloro-3-(trifluoromethyl)benzyl)-6,7-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-8(5H)-one

HRID 576710Notes

Reaction equation

HRID 576710 reaction equation
[Br:1][C:2]1[N:6]2[CH2:7][CH2:8][NH:9][C:10](=[O:11])[C:5]2=[N:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[C:21]=1[Cl:30]>CN(C=O)C>[Br:1][C:2]1[N:6]2[CH2:7][CH2:8][N:9]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:29])[F:28])[C:21]=3[Cl:30])[C:10](=[O:11])[C:5]2=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27788481-(Bromomethyl)-2-chloro-3-(trifluoromethyl)benzeneHCID 90402511HCID 90402511, compound

Product 1

HCID 904024003-bromo-7-(2-chloro-3-(trifluoromethyl)benzyl)-6,7-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-8(5H)-oneYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a slurry of 3-bromo-6,7-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-8(5H)-one (294 mg, 1.4 mmol) and cesium carbonate (1.32 g, 4.1 mmol) in DMF (10 mL) was added 1-(bromomethyl)-2-chloro-3-(trifluoromethyl)benzene (446 mg, 1.6 mmol). After 5 h, the reaction mixture was poured into ice cold brine (200 mL). The resulting precipitate was filtered and washed successively with water and ether to provide the product as a white solid (456 mg, 82%). MS (ESI): mass calcd. for C13H9BrClF3N4O, 408.0; m/z found, 409.0 [M+H]+. 1H NMR (500 MHz, DMSO-d6) δ 7.82 (d, J=7.6 Hz, 1H), 7.77 (d, J=7.6 Hz, 1H), 7.55 (t, J=7.8 Hz, 1H), 4.85 (s, 2H), 4.36-4.24 (m, 2H), 3.99-3.83 (m, 2H).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed successively with water and ether

Sources & evidence

ORD record
ord-90f82553e4b143f28c3e5359ecff151e
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Reaction notes

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