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

HRID 878546Notes

Reaction equation

HRID 878546 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-0560632cf6ba47b99b069c92a2b828db
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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