1-Bromo-3-(bromomethyl)-5-fluorobenzene → 2-(3-Bromo-5-fluorobenzyl)-5-(4-chlorophenyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714659Notes

Reaction equation

HRID 714659 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:14][C@H: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.[Br:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([CH2:29]Br)[CH:23]=1>>[Br:21][C:22]1[CH:23]=[C:24]([CH:25]=[C:26]([F:28])[CH:27]=1)[CH2:29][N:11]1[C:10](=[O:13])[N:9]([CH2:14][C@H: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

3

Reactant 2

HCID 235096191-Bromo-3-(bromomethyl)-5-fluorobenzeneHCID 595368365-(4-Chlorophenyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 866909142-(3-Bromo-5-fluorobenzyl)-5-(4-chlorophenyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Procedure

219 mg (0.71 mmol) of the compound from Example 5A and 191 mg (0.71 mmol) of 1-bromo-3-(bromomethyl)-5-fluorobenzene were reacted analogously to the preparation of Example 101A. This gave 181 mg (51% of theory) of the target compound.

Sources & evidence

ORD record
ord-78f6af7f70204119abec89a6ec514c3c
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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