(2E)-1-(4-Bromophenyl)-3-(dimethylamino)-2-propen-1-one → HCID 86725516, compound

HRID 514388Notes

Reaction equation

HRID 514388 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)/[CH:9]=[CH:10]/[N:11](C)C)=[CH:4][CH:3]=1.Cl.[NH:16]([C:18]1[CH:23]=[C:22]([C:24]#[N:25])[CH:21]=[CH:20][N:19]=1)N>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([C:18]3[CH:23]=[C:22]([C:24]#[N:25])[CH:21]=[CH:20][N:19]=3)[N:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 5376915(2E)-1-(4-Bromophenyl)-3-(dimethylamino)-2-propen-1-oneHCID 867254842-Hydrazinylpyridine-4-carbonitrile hydrochloride salt

Product 1

HCID 86725516HCID 86725516, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (2E)-1-(4-bromophenyl)-3-(dimethylamino)prop-2-en-1-one (100 mg, 0.39 mmol) and 2-hydrazinylpyridine-4-carbonitrile hydrochloride salt (90 mg, 0.43 mmol, PREPARATION 3) in MeOH (10 mL) was heated under reflux conditions for 30 min and then cooled to rt. The solution was concentrated, and the residue was purified by flash column chromatography (hexanes:EtOAc=1:1) to give the title compound (108 mg, 85%) as an orange-yellow solid.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was purified by flash column chromatography (hexanes:EtOAc=1:1)

Sources & evidence

ORD record
ord-a382c830bc1c49258b8395690efea1d0
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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