2-Chlorophenylboronic acid → 2-[(2'-Chloro-5-fluorobiphenyl-3-yl)methyl]-5-(4-chlorophenyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxy-propyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714731Notes

Reaction equation

HRID 714731 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:26]=[C:27]([F:29])[CH:28]=1)[CH2:5][N:6]1[C:10](=[O:11])[N:9]([CH2:12][C@H: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.[Cl:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1B(O)O>>[Cl:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:2]1[CH:28]=[C:27]([F:29])[CH:26]=[C:4]([CH2:5][N:6]2[C:10](=[O:11])[N:9]([CH2:12][C@H:13]([OH:18])[C:14]([F:16])([F:17])[F:15])[C:8]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)=[N:7]2)[CH:3]=1

Participants

3

Reactant 2

HCID 27343222-Chlorophenylboronic acidHCID 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

Product 1

HCID 866909402-[(2'-Chloro-5-fluorobiphenyl-3-yl)methyl]-5-(4-chlorophenyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxy-propyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

Procedure

Analogously to the preparation of Example 122, 59 mg (0.12 mmol) of the compound from Example 103A were reacted with 28 mg (0.18 mmol) of 2-chlorophenylboronic acid. This gave 34 mg (54% of theory) of the target compound.

Sources & evidence

ORD record
ord-6b1ddafe95084821a3b2554e270e2697
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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