4-Fluorobenzyl bromide → methyl 2-(1-(cyclopropylmethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinate

HRID 714296Notes

Reaction equation

HRID 714296 reaction equation
BrCC1C=CC(F)=CC=1.Br[CH2:11][CH:12]1[CH2:14][CH2:13]1.[O:15]=[C:16]1[NH:20][N:19]=[CH:18][N:17]1[C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][N:30]=1)[C:24]([O:26][CH3:27])=[O:25]>>[CH:14]1([CH2:13][N:20]2[C:16](=[O:15])[N:17]([C:21]3[CH:22]=[C:23]([CH:28]=[CH:29][N:30]=3)[C:24]([O:26][CH3:27])=[O:25])[CH:18]=[N:19]2)[CH2:12][CH2:11]1

Participants

4

Reactant 3

HCID 680214-Fluorobenzyl bromideHCID 81503BromomethylcyclopropaneHCID 58247755methyl 2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinate

Product 1

HCID 58247813methyl 2-(1-(cyclopropylmethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinateYield 65%

Procedure

Following the procedure as described in Preparation 17, making variations as required to replace 1-(bromomethyl)-4-fluorobenzene with (bromomethyl)cyclopropane to react with methyl 2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinate, methyl 2-(1-(cyclopropylmethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinate was obtained as a colorless solid in 65% yield: MS (ES+) m/z 275.1 (M+1).

Workup

  1. customas described in Preparation 17

Sources & evidence

ORD record
ord-6f69a4462ba148288c692051928d899a
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

Loading…