Potassium Carbonate → 3-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-yl)-acrylic Acid Ethyl Ester

HRID 11682Notes

Reaction equation

HRID 11682 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=O)[C:5]([O:8][CH2:9][C:10]([N:12]2[CH2:17][CH:16]([CH3:18])[N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:14][CH:13]2[CH3:27])=[O:11])=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[C:36]([O-:39])(=[O:38])[CH3:37].[CH2:40]([PH+](CC)CC)[CH3:41]>C(O)C.O>[CH2:40]([O:38][C:36](=[O:39])[CH:37]=[CH:28][C:4]1[C:5]([O:8][CH2:9][C:10]([N:12]2[CH2:17][C@H:16]([CH3:18])[N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:14][C@H:13]2[CH3:27])=[O:11])=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH3:41]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 219733105-Chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridine-3-carbaldehydeHCID 21973468Triethylphosphonium acetate

Product 1

HCID 696553743-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-yl)-acrylic Acid Ethyl EsterYield 44.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a 0° C. solution of 5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridine-3-carbaldehyde (0.200 g, 0.47 mmol) in ethanol (5 mL) was added potassium carbonate (0.131 g, 0.95 mmol) in water (0.30 mL) and triethyl phosphonium acetate (0.21 g, 0.19 mL). The reaction mixture was warmed to room temperature over 48 hours, filtered through celite, the filter cake was washed with ethanol and concentrated in vacuo. Purification via chromatography on silica gel gave the title compound (0.102 g).

Workup

  1. filtrationfiltered through celite
  2. washthe filter cake was washed with ethanol
  3. concentrationconcentrated in vacuo
  4. customPurification via chromatography on silica gel

Sources & evidence

ORD record
ord-749a9b298e704c3cbd3759170ce98838
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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