N-bromobutanimide → 2-Bromo-1-(6-bromoquinolin-2-yl)ethanone

HRID 625626Notes

Reaction equation

HRID 625626 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[Br:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[C:15]([C:20]([O:22]CC)=[CH2:21])[CH:14]=[CH:13]2>C1COCC1.O>[Br:8][CH2:22][C:20]([C:15]1[CH:14]=[CH:13][C:12]2[C:17](=[CH:18][CH:19]=[C:10]([Br:9])[CH:11]=2)[N:16]=1)=[O:21]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 584987316-Bromo-2-(1-ethoxyvinyl)quinoline

Product 1

HCID 584988992-Bromo-1-(6-bromoquinolin-2-yl)ethanoneYield 60.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

NBS (407 mg, 2.287 mmol) was added to a solution of 6-bromo-2-(1-ethoxyvinyl)quinoline (530 mg, 1.91 mmol) in THF (10 mL) and water (2.5 mL) and the mixture was stirred at rt for 2 h. The reaction mixture was partitioned between EtOAc and brine and the organic layer was concentrated. The crude material was purified by flash silica gel chromatography (eluted with Et2O/hexanes, gradient from 0 to 5% Et2O) to yield 2-bromo-1-(6-bromoquinolin-2-yl)ethanone (380 mg) as white solid. LC-MS retention time 3.988 min; m/z 329.84 (MH+). LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a PHENOMENEX® Luna 3u C18 2.0×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 0.8 mL/min, a gradient of 100% Solvent A/0% Solvent B to 0% Solvent A/100% Solvent B, a gradient time of 4 min, a hold time of 1 min, and an analysis time of 5 min where Solvent A was 10% MeOH/90% H2O/0.1% trifluoroacetic acid and Solvent B was 10% H2O/90% MeOH/0.1% trifluoroacetic acid. MS data was determined using a MICROMASS® Platform for LC in electrospray mode.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and brine
  2. concentrationthe organic layer was concentrated
  3. customThe crude material was purified by flash silica gel chromatography (eluted with Et2O/hexanes, gradient from 0 to 5% Et2O)

Sources & evidence

ORD record
ord-1bcd84e71d60479ba1a20514334fd57c
Source dataset
uspto-grants-2016_04
Patent number
US09303007B2

Reaction notes

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