Potassium Carbonate → HCID 59643273, compound

HRID 2251535Notes

Reaction equation

HRID 2251535 reaction equation
[CH3:1][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]([F:30])([F:29])[F:28])=[CH:22][CH:21]=2)=[CH:12][CH:11]=1)([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].Cl[C:32]1[CH:39]=[CH:38][C:35]([CH:36]=[O:37])=[CH:34][N:33]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:36]([C:35]1[CH:38]=[CH:39][C:32]([N:18]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][C:27]([F:28])([F:29])[F:30])=[CH:24][CH:25]=2)[CH2:17][CH2:16][C:13]2[CH:14]=[CH:15][C:10]([O:9][C:2]([CH3:1])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:11][CH:12]=2)=[N:33][CH:34]=1)=[O:37]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27640536-Chloropyridine-3-carbaldehydeHCID 59643426Ethyl 2-methyl-2-[4-(2-{[4-(trifluoromethoxy)benzyl]amino}ethyl)phenoxy]propanoate

Product 1

HCID 59643273HCID 59643273, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 2-methyl-2-[4-(2-{[4-(trifluoromethoxy)benzyl]amino}ethyl)phenoxy]propanoate (3.0 g; 7.05 mmol) in 8 ml of DMF was treated with 6-chloronicotinaldehyde (0.91 g; 6.42 mmol) and K2CO3 (0.97 g; 7.05 mmol). The reaction mixture was heated at 150C for 4 hr. Upon cooling, the mixture was partitioned between ethyl acetate and 0.05N HCl. The organic phase was washed with 0.05N HCl and brine, dried over sodium sulfate, filtered and concentrated. Purification by flash chromatography using ethyl acetate-hexane mixtures (5–50%) afforded the title compound (2.3 g; 68% yield).

Workup

  1. temperatureUpon cooling
  2. customthe mixture was partitioned between ethyl acetate and 0.05N HCl
  3. washThe organic phase was washed with 0.05N HCl and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-2a579af4adec40989e5b5613fd1ddca0
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

Loading…