2-(Trifluoromethyl)benzeneboronic acid → 5-(4-Chlorophenyl)-4-(3,3,3-trifluoro-2-hydroxypropyl)-2-{[2'-(trifluoromethyl)biphenyl-3-yl]-methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714728Notes

Reaction equation

HRID 714728 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[CH2:5][N:6]1[C:10](=[O:11])[N:9]([CH2:12][CH:13]([OH:18])[C:14]([F:17])([F:16])[F:15])[C:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[N:7]1.[F:29][C:30]([F:41])([F:40])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1B(O)O>>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:8]2[N:9]([CH2:12][CH:13]([OH:18])[C:14]([F:17])([F:16])[F:15])[C:10](=[O:11])[N:6]([CH2:5][C:4]3[CH:3]=[C:2]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=4[C:30]([F:41])([F:40])[F:29])[CH:28]=[CH:27][CH:26]=3)[N:7]=2)=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 699397432-(3-Bromobenzyl)-5-(4-chlorophenyl)-4-(3,3,3-trifluoro-2-hydroxypropyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 866909375-(4-Chlorophenyl)-4-(3,3,3-trifluoro-2-hydroxypropyl)-2-{[2'-(trifluoromethyl)biphenyl-3-yl]-methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

Procedure

Analogously to the preparation of Example 122, 72 mg (0.15 mmol) of the compound from Example 101A were reacted with 43 mg (0.23 mmol) of 2-(trifluoromethyl)phenylboronic acid. This gave 49 mg (58% of theory) of the target compound.

Sources & evidence

ORD record
ord-94edc3be9e8e4952a51722404182d8ac
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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