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

HRID 714730Notes

Reaction equation

HRID 714730 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.[F:30][C:31]([F:42])([F:41])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1B(O)O>>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:8]2[N:9]([CH2:12][C@H: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:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[C:31]([F:42])([F:41])[F:30])[CH:28]=[C:27]([F:29])[CH:26]=3)[N:7]=2)=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 27343872-(Trifluoromethyl)benzeneboronic 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 866909395-(4-Chlorophenyl)-2-{[5-fluoro-2'-(trifluoromethyl)biphenyl-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 Example 122, 59 mg (0.12 mmol) of the compound from Example 103A were reacted with 36 mg (0.18 mmol) of 2-(trifluoromethyl)phenylboronic acid. This gave 43 mg (64% of theory) of the target compound.

Sources & evidence

ORD record
ord-b6d20f2fd17340c8a6c393e7e63bc5f9
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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