1H-1,2,4-Triazole → HCID 25254686, compound

HRID 219462Notes

Reaction equation

HRID 219462 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[C:10]([O:11][CH2:12][CH2:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH3:15])=[C:9]([O:23][CH3:24])[C:8]([Cl:25])=[C:7]([CH3:26])[C:6]=1[C:27](=[O:29])[CH3:28].[NH:30]1[CH:34]=[N:33][CH:32]=[N:31]1>>[Cl:25][C:8]1[C:7]([CH3:26])=[C:6]([C:27](=[O:29])[CH3:28])[C:5]([O:4][CH2:3][CH2:2][N:30]2[CH:34]=[N:33][CH:32]=[N:31]2)=[C:10]([O:11][CH2:12][CH2:13][CH:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH3:15])[C:9]=1[O:23][CH3:24]

Participants

3

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 595835231-{2-(2-Bromo-ethoxy)-5-chloro-3-[3-(4-fluoro-phenyl)-butoxy]-4-methoxy-6-methyl-phenyl}-ethanone

Product 1

HCID 25254686HCID 25254686, compoundYield 72%

Procedure

Example 8a (85 mg, 0.17 mmol) was reacted with 1,2,4-triazole (2.5 eq.) and CsCO3 (1.94 eq.) as described under General Procedure L and the crude mixture was purified by flash chromatography (silica gel, Et2O) to afford the title compound as a pale yellow oil (58 mg, 72%). 1H NMR (300 MHz, CDCl3) δ 8.12 (s, 1H), 7.95 (s, 1H), 7.17 (m, 2H), 7.01-6.95 (m, 2H), 4.39-4.36 (m, 4H), 3.83-3.78 (m, 5H), 2.91 (m, 1H), 2.32 (s, 3H), 2.16 (s, 3H), 1.94-1.89 (m, 2H), 1.27 (d, J=6.9 Hz, 3H). MS (ES+) m/z 476.2 (M+H+).

Workup

  1. customthe crude mixture was purified by flash chromatography (silica gel, Et2O)

Sources & evidence

ORD record
ord-ae76f72336c4456dabff468bf231261b
Source dataset
uspto-grants-2012_06
Patent number
US08202513B2

Reaction notes

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