Ethyl Bromide → 1-(4-((3-Chloro-2-fluorophenyl)ethynyl)phenyl)-3-(2-chloro-6-fluorophenyl)-4-ethyl-1H-1,2,4-triazol-5(4H)-one

HRID 59485Notes

Reaction equation

HRID 59485 reaction equation
[Cl:1][C:2]1[C:3]([F:30])=[C:4]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:20](=[O:21])[NH:19][C:18]([C:22]4[C:27]([F:28])=[CH:26][CH:25]=[CH:24][C:23]=4[Cl:29])=[N:17]3)=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH2:33](Br)[CH3:34]>CN(C=O)C>[Cl:1][C:2]1[C:3]([F:30])=[C:4]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[C:20](=[O:21])[N:19]([CH2:33][CH3:34])[C:18]([C:22]4[C:27]([F:28])=[CH:26][CH:25]=[CH:24][C:23]=4[Cl:29])=[N:17]3)=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 1364924271-(4-((3-Chloro-2-fluorophenyl)ethynyl)phenyl)-3-(2-chloro-6-fluorophenyl)-1H-1,2,4-triazol-5(4H)-one

Product 1

HCID 900263411-(4-((3-Chloro-2-fluorophenyl)ethynyl)phenyl)-3-(2-chloro-6-fluorophenyl)-4-ethyl-1H-1,2,4-triazol-5(4H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared by following the procedure as described for Intermediate-41 by using 1-(4-((3-chloro-2-fluorophenyl)ethynyl)phenyl)-3-(2-chloro-6-fluorophenyl)-1H-1,2,4-triazol-5(4H)-one (Example-12, 0.070 g, 0.15 mmol), dry DMF (3 mL), NaH (0.010 g, 0.23 mmol) and ethyl bromide (0.026 g, 0.23 mmol) to afford 0.030 g of the crude product which was purified by column chromatography in basic alumina eluting with 0.2% methanol:DCM to afford 0.030 g of pure product. 1H NMR (300 MHz, DMSO d6): δ 1.09 (t, 3H), 3.56 (m, 2H), 7.29 (t, 1H), 7.52-7.84 (m, 7H), 8.04 (d, J=8.1 Hz, 2H); MS (m/z): 470.06 (M+H)+.

Workup

  1. customto afford 0.030 g of the crude product which

Sources & evidence

ORD record
ord-438830c3b08b461c92c88706ffd3255b
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

Loading…