Potassium Carbonate → HCID 117864695, compound

HRID 1486326Notes

Reaction equation

HRID 1486326 reaction equation
CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[NH2:14][N+:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][C:16]=1[O:23][CH2:24][C:25]1[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=1[F:32].[C:33]([O:38][CH2:39][CH3:40])(=[O:37])[C:34]#[C:35][CH3:36].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:39]([O:38][C:33]([C:34]1[C:35]([CH3:36])=[N:14][N:15]2[C:16]([O:23][CH2:24][C:25]3[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=3[F:32])=[CH:17][C:18]([CH2:21][CH3:22])=[CH:19][C:20]=12)=[O:37])[CH3:40]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 78043Ethyl 2-butynoateHCID 117858293HCID 117858293, compound

Product 1

HCID 117864695HCID 117864695, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.88 g (1.54 mmol, 38% purity) of 1-amino-2-[(2,6-difluorobenzyl)oxy]-4-ethylpyridinium 2,4,6-trimethylbenzenesulphonate (Example 166A) in 12 ml of N,N-Dimethylformamide was admixed with 0.35 g (3.08 mmol) of ethyl 2-butynoate (CAS: 4341-76-8) and 0.64 g (4.61 mmol) of potassium carbonate. The reaction mixture was stirred at room temperature for 3 hours. The solvent was concentrated and the residue was partitioned between water and ethyl acetate. The organic phase was removed, washed with aqueous sodium chloride solution and concentrated under reduced pressure. The residue was purified by flash chromatography using a prepacked silica gel cartridge (eluent:cyclohexane/ethyl acetate, gradient 0% to 10%), which gave 0.29 g (35% yield, 70% purity) of product.

Workup

  1. concentrationThe solvent was concentrated
  2. customthe residue was partitioned between water and ethyl acetate
  3. customThe organic phase was removed
  4. washwashed with aqueous sodium chloride solution
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography
  7. customgave 0.29 g (35% yield, 70% purity) of product

Sources & evidence

ORD record
ord-5dee1f64308a44e190226345f7cb3589
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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