2,3-Dichlorobenzeneboronic acid → Methyl 2',3'-dichloro-3-({3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}methyl)biphenyl-4-carboxylate

HRID 714735Notes

Reaction equation

HRID 714735 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:12][N:13]2[C:17](=[O:18])[N:16]([CH2:19][C@H:20]([OH:25])[C:21]([F:24])([F:23])[F:22])[C:15]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)=[N:14]2)[CH:3]=1.[Cl:33][C:34]1[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][C:35]=1B(O)O>>[Cl:33][C:34]1[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][C:35]=1[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:12][N:13]2[C:17](=[O:18])[N:16]([CH2:19][C@H:20]([OH:25])[C:21]([F:22])([F:24])[F:23])[C:15]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)=[N:14]2)[CH:3]=1

Participants

3

Reactant 2

HCID 27346612,3-Dichlorobenzeneboronic acidHCID 67396533Methyl 4-bromo-2-({3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}methyl)benzoate

Product 1

HCID 86690943Methyl 2',3'-dichloro-3-({3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}methyl)biphenyl-4-carboxylate

Procedure

Analogously to the preparation of Example 75, 455 mg (0.85 mmol) of the compound from Example 105A were reacted with 244 mg (1.28 mmol) of 2,3-dichlorophenylboronic acid. This gave 347 mg (57% of theory) of the target compound.

Sources & evidence

ORD record
ord-d84b7be23ec34244ab359fa3461866e8
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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