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

HRID 714297Notes

Reaction equation

HRID 714297 reaction equation
O=C1NCCN1C1C=C(C=CN=1)C([O-])=O.[O:16]=[C:17]1[NH:21][N:20]=[CH:19][N:18]1[C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][N:31]=1)[C:25]([O:27][CH3:28])=[O:26].Br[CH2:33][C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1>>[F:40][C:37]1[CH:38]=[CH:39][C:34]([CH2:33][N:21]2[C:17](=[O:16])[N:18]([C:22]3[CH:23]=[C:24]([CH:29]=[CH:30][N:31]=3)[C:25]([O:27][CH3:28])=[O:26])[CH:19]=[N:20]2)=[CH:35][CH:36]=1

Participants

4

Reactant 3

HCID 680214-Fluorobenzyl bromideHCID 58247755methyl 2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinateHCID 866530512-(2-Oxoimidazolidin-1-yl)isonicotinate

Product 1

HCID 58247815methyl 2-(1-(4-fluorobenzyl)-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 2-(2-oxoimidazolidin-1-yl)isonicotinate with methyl 2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinate to react with 1-(bromomethyl)-4-fluorobenzene, methyl 2-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinate was obtained as a colorless solid in 65% yield: MS (ES+) m/z 328.9 (M+1).

Workup

  1. customas described in Preparation 17

Sources & evidence

ORD record
ord-2f75310ec1854f20b67a90b0eaf1a1b6
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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