Acetonitrile → HCID 58452310, compound

HRID 70529Notes

Reaction equation

HRID 70529 reaction equation
C(#N)C.[C:4]([C:8]1[CH:13]=[CH:12][C:11](/[C:14](/[C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([O:26][CH3:27])[N:20]=2)=[CH:15]\C(O)=O)=[CH:10][CH:9]=1)([CH3:7])([CH3:6])[CH3:5].[Br:28]N1C(=O)CCC1=O>C(N(CC)CC)C>[Br:28]/[CH:15]=[C:14](/[C:19]1[N:20]=[C:21]([O:26][CH3:27])[C:22]([Cl:25])=[CH:23][CH:24]=1)\[C:11]1[CH:12]=[CH:13][C:8]([C:4]([CH3:7])([CH3:6])[CH3:5])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 67184N-bromobutanimideHCID 58452337(2E)-3-(4-tert-Butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-enoic acid

Product 1

HCID 58452310HCID 58452310, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A 97% acetonitrile solution (52 mL) containing triethylamine (26 μL) was added to (2E)-3-(4-tert-butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-enoic acid (1.3 g). N-bromosuccinimide (806 mg) was added thereto and the mixture was stirred at room temperature for 15 minutes. The solvent was evaporated under reduced pressure from the reaction solution. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1) to give the title compound as a colorless powder (363 mg, 25%).

Workup

  1. customThe solvent was evaporated under reduced pressure from the reaction solution
  2. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1)

Sources & evidence

ORD record
ord-3967e97791ca43dfbfb76ec8b4b55a3d
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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