Methyl 3-(bromomethyl)benzoate → Methyl 3-{[3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoro-2-hydroxypropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}benzoate

HRID 536544Notes

Reaction equation

HRID 536544 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][CH:14]([OH:19])[C:15]([F:18])([F:17])[F:16])[C:11](=[O:20])[N:10]([CH2:21]C3C=CC(C(OC)=O)=CC=3)[N:9]=2)=[CH:4][CH:3]=1.ClC1C=CC(C2N(CC(O)C(F)(F)F)C(=O)NN=2)=CC=1.BrC[C:54]1[CH:55]=[C:56]([CH:61]=[CH:62][CH:63]=1)[C:57]([O:59][CH3:60])=[O:58]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH2:13][CH:14]([OH:19])[C:15]([F:18])([F:16])[F:17])[C:11](=[O:20])[N:10]([CH2:21][C:54]3[CH:55]=[C:56]([CH:61]=[CH:62][CH:63]=3)[C:57]([O:59][CH3:60])=[O:58])[N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 517981Methyl 3-(bromomethyl)benzoateHCID 58460117Methyl 4-{[3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoro-2-hydroxypropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}benzoateHCID 584601185-(4-Chlorophenyl)-4-(3,3,3-trifluoro-2-hydroxypropyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 58460127Methyl 3-{[3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoro-2-hydroxypropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]methyl}benzoate

Procedure

In the same way as for the compound from Example 24A, 267 mg (0.87 mmol) of the compound from Example 19A were reacted with 199 mg (0.87 mmol) of methyl 3-(bromomethyl)benzoate. This gave 302 mg (76% of theory) of the target compound.

Sources & evidence

ORD record
ord-5951548bd4f449248b3f3f472093d770
Source dataset
uspto-grants-2014_10
Patent number
US08859601B2

Reaction notes

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