Sodium Carbonate → HCID 86762124, compound

HRID 2040848Notes

Reaction equation

HRID 2040848 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]([N+:14]([O-:16])=[O:15])[C:4](=C)[CH:3]=1.[C:18](=O)([O-])[O-].[Na+].[Na+].[Br:24][C:25](Br)=[N:26][OH:27]>CCOC(C)=O>[Br:24][C:25]1[CH2:18][C:11]2([CH2:10][CH2:9][N:8]([C:6]3[C:5]([N+:14]([O-:16])=[O:15])=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=3)[CH2:13][CH2:12]2)[O:27][N:26]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27632191-bromo-N-hydroxymethanecarbonimidoyl bromideHCID 66603726HCID 66603726, compound2×

Product 1

HCID 86762124HCID 86762124, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 1-(6-methyl-4-methylen-3-nitro-2-pyridyl)piperidine (Compound 3a, 350 mg, 1.5 mmol), sodium carbonate (1.26 g, 15 mmol) and dibromoformaldoxime (608 mg, 3 mmol) in 25 mL of EtOAc was stirred at r.t. for 2 days. Afterwards, the reaction mixture was washed with water, dried over sodium sulphate and evaporated to dryness in vacuo. The crude was purified by automated flash chromatography (SP1®TM-Biotage; gradient Petroleum Ether-EtOAc from 9:1 to 6:4) giving 377 mg of the title product. Yield: 70.8%.

Workup

  1. washAfterwards, the reaction mixture was washed with water
  2. dry with materialdried over sodium sulphate
  3. customevaporated to dryness in vacuo
  4. customThe crude was purified by automated flash chromatography (SP1®TM-Biotage; gradient Petroleum Ether-EtOAc from 9:1 to 6:4)

Sources & evidence

ORD record
ord-e87f3fcddc2c42b7a21f71b79adeb0a8
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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