Allyl bromide → 1-Allyl-3-benzyloxy-5-(4-fluoro-benzylcarbamoyl)-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid methyl ester

HRID 1931216Notes

Reaction equation

HRID 1931216 reaction equation
Br[CH2:2][CH:3]=[CH2:4].[CH3:5][O:6][C:7]([C:9]1[C:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:13]([OH:23])[C:12]([C:24](=[O:34])[NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:11][N:10]=1)=[O:8].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[NH4+]>CN(C)C=O>[CH3:5][O:6][C:7]([C:9]1[N:10]([CH2:4][CH:3]=[CH2:2])[CH:11]=[C:12]([C:24](=[O:34])[NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[C:13](=[O:23])[C:14]=1[O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:8]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 178499094HCID 178499094, compound

Product 1

HCID 596005921-Allyl-3-benzyloxy-5-(4-fluoro-benzylcarbamoyl)-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid methyl esterYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After 3-bromopropene (2.15 ml, 24.8 mmol) was added to a solution of the compound 14 (6.79 g, 16.5 mmol), and cesium carbonate (8.09 g, 24.8 mmol) in dimethylformamide (54 ml), the mixture was stirred at room temperature for 4.5 hours. To the reaction solution was added an aqueous ammonium chloride solution, and this was extracted with ethyl acetate, washed with water and an aqueous saturated sodium chloride solution, and dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was washed with diethyl ether to obtain 1-allyl-3-benzyloxy-5-(4-fluoro-benzylcarbamoyl)-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid methyl ester 15 (6.15 g, 83%) as a colorless crystal.

Workup

  1. extractionthis was extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialan aqueous saturated sodium chloride solution, and dried with anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. washthe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-d8666e535fe14cc99f21090473d0ce17
Source dataset
uspto-grants-2012_05
Patent number
US08188271B2

Reaction notes

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