(2-Hydroxyphenyl)boronic acid → Methyl [4-(3-fluorobenzyl)-3-(2-hydroxyphenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

HRID 660884Notes

Reaction equation

HRID 660884 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][N:5]1[C:9](=[O:10])[N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[C:7](Br)=[N:6]1.[OH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O>>[CH3:1][O:2][C:3](=[O:20])[CH2:4][N:5]1[C:9](=[O:10])[N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[C:7]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[OH:21])=[N:6]1

Participants

3

Reactant 2

HCID 2773454(2-Hydroxyphenyl)boronic acidHCID 58011964Methyl [3-bromo-4-(3-fluorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

Product 1

HCID 136199106Methyl [4-(3-fluorobenzyl)-3-(2-hydroxyphenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-acetate

Procedure

By the method described for Example 147A, starting from 250 mg (0.73 mmol) of the compound from Example 146A and 138 mg of (1.02 mmol) 2-hydroxyphenylboronic acid, 22 mg (8% of theory) of the title compound and 222 mg (85% of theory) of the corresponding acid formed by hydrolysis (see also Example 150A) are obtained.

Sources & evidence

ORD record
ord-5e1df18c33af4badb8414f6e791db7dd
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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