2-Chlorophenylboronic acid → 5-(4-Chlorophenyl)-2-{[5-(2-chlorophenyl)pyridin-3-yl]methyl}-4-(3,3,3-trifluoro-2-hydroxypropyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714699Notes

Reaction equation

HRID 714699 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][N:9]2[C:13](=[O:14])[N:12]([CH2:15][CH:16]([OH:21])[C:17]([F:20])([F:19])[F:18])[C:11]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)=[N:10]2)[CH:5]=[N:6][CH:7]=1.[Cl:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1B(O)O>>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([C:11]2[N:12]([CH2:15][CH:16]([OH:21])[C:17]([F:20])([F:19])[F:18])[C:13](=[O:14])[N:9]([CH2:8][C:4]3[CH:5]=[N:6][CH:7]=[C:2]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=4[Cl:29])[CH:3]=3)[N:10]=2)=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 27343222-Chlorophenylboronic acidHCID 674086672-[(5-Bromopyridin-3-yl)methyl]-5-(4-chlorophenyl)-4-(3,3,3-trifluoro-2-hydroxypropyl)-2,4-di-hydro-3H-1,2,4-triazol-3-one

Product 1

HCID 533788415-(4-Chlorophenyl)-2-{[5-(2-chlorophenyl)pyridin-3-yl]methyl}-4-(3,3,3-trifluoro-2-hydroxypropyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Procedure

Analogously to the preparation of the compound in Example 86, 72 mg (0.15 mmol) of the compound from Example 28A and 59 mg (0.23 mmol) of 2-chlorophenylboronic acid were reacted with one another. This gave 49 mg (64% of theory) of the target compound.

Workup

  1. customwere reacted with one another

Sources & evidence

ORD record
ord-88794f1de0e64855bdb965f5181a7b99
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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