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

HRID 714391Notes

Reaction equation

[O:1]=[C:2]1[NH:6][N:5]=[CH:4][N:3]1[C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][N:16]=1)[C:10]([O:12][CH3:13])=[O:11].[H-].[Na+].Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1>CN(C)C=O>[F:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:6]2[C:2](=[O:1])[N:3]([C:7]3[CH:8]=[C:9]([CH:14]=[CH:15][N:16]=3)[C:10]([O:12][CH3:13])=[O:11])[CH:4]=[N:5]2)=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinate (1.68 g, 7.63 mmol) in N,N-dimethylformamide (76 mL) was added sodium hydride (60% dispersion in mineral oil, 0.67 g, 16.80 mmol) at 0° C. The resulting reaction mixture was stirred for 1 hour at 0° C., followed by the addition of 1-(bromomethyl)-4-fluorobenzene (3.23 g, 17.09 mmol) dropwise. The reaction mixture was stirred at ambient temperature for 48 hours and concentrated in vacuo to dryness to give methyl 2-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)isonicotinate, and used in the further reaction without purification

Workup

customThe resulting reaction mixture
stirringThe reaction mixture was stirred at ambient temperature for 48 hours
concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record: ord-3d61d17c314c4c9da60c26a91c6b4e46
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187426B2

Reaction notes

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