Cesium carbonate → 2-(3-Bromobenzyl)-5-(4-chlorophenyl)-4-(3,3,3-trifluoro-2-hydroxypropyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714658Notes

Reaction equation

HRID 714658 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:14][CH:15]([OH:20])[C:16]([F:19])([F:18])[F:17])[C:10](=[O:13])[NH:11][N:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31]Br>C(#N)C>[Br:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31][N:11]1[C:10](=[O:13])[N:9]([CH2:14][CH:15]([OH:20])[C:16]([F:18])([F:19])[F:17])[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:12]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 699793-Bromobenzyl bromideHCID 584601185-(4-Chlorophenyl)-4-(3,3,3-trifluoro-2-hydroxypropyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 699397432-(3-Bromobenzyl)-5-(4-chlorophenyl)-4-(3,3,3-trifluoro-2-hydroxypropyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

400 mg (1.30 mmol) of the compound from Example 4A and 635 mg (1.95 mmol) of cesium carbonate were suspended in 3 ml of acetonitrile, and 357 mg (1.43 mmol) of 3-bromobenzyl bromide were added. The mixture was stirred under reflux for 20 h. The precipitated solid was then filtered off, and the filtrate was concentrated under reduced pressure to a volume of about 1.5 ml and directly purified chromatographically [Method 19]. This gave 507 mg (82% of theory) of the target compound.

Workup

  1. temperatureunder reflux for 20 h
  2. filtrationThe precipitated solid was then filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure to a volume of about 1.5 ml
  4. customdirectly purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-b65e7fb987b547a898e64b6f0f8aecd2
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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