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

HRID 714700Notes

Reaction equation

HRID 714700 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][N:9]2[C:13](=[O:14])[N:12]([CH2:15][C@H: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[C:35]([Cl:36])=[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][C@H: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:34]4[CH:33]=[CH:32][CH:31]=[C:30]([Cl:29])[C:35]=4[Cl:36])[CH:3]=3)[N:10]=2)=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 27346612,3-Dichlorobenzeneboronic acidHCID 673972232-[(5-Bromopyridin-3-yl)methyl]-5-(4-chlorophenyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 866909265-(4-Chlorophenyl)-2-{[5-(2,3-dichlorophenyl)pyridin-3-yl]methyl}-4-[(2S)-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, 34 mg (0.07 mmol) of the compound from Example 29A and 20 mg (0.10 mmol) of 2,3-dichlorophenylboronic acid were reacted with one another. This gave 26 mg (69% of theory) of the target compound.

Workup

  1. customwere reacted with one another

Sources & evidence

ORD record
ord-ea2bd653bcda4296b66795a573444988
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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