Water → Ethyl 2,6-dimethyl-8-[4,4,4-trifluoro-3-(trifluoromethyl)butoxy]imidazo[1,2-a]pyridine-3-carboxylate

HRID 1624109Notes

Reaction equation

HRID 1624109 reaction equation
[OH:1][C:2]1[C:3]2[N:4]([C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:24][C:25]([F:35])([F:34])[CH:26]([C:30]([F:33])([F:32])[F:31])[CH2:27][CH2:28]Br.O>CN(C=O)C>[CH3:12][C:10]1[N:11]=[C:3]2[C:2]([O:1][CH2:28][CH2:27][CH:26]([C:25]([F:24])([F:34])[F:35])[C:30]([F:31])([F:33])[F:32])=[CH:7][C:6]([CH3:8])=[CH:5][N:4]2[C:9]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27779984-Bromo-1,1,1-trifluoro-2-(trifluoromethyl)butaneHCID 86717883Ethyl 8-hydroxy-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 86717933Ethyl 2,6-dimethyl-8-[4,4,4-trifluoro-3-(trifluoromethyl)butoxy]imidazo[1,2-a]pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.89 g (8.07 mmol) of ethyl 8-hydroxy-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate Example 87A were initially charged in 60 ml of DMF, 7.89 g (24.2 mmol) of caesium carbonate and 2.30 g (8.88 mmol) of 4,4,4-trifluoro-3-(trifluoromethyl)butyl bromide were added and the reaction mixture was stirred at RT for 90 min. 60 ml of water were then added, the precipitated solid was filtered off and the filter residue was washed with 100 ml of water and twice with 20 ml of tert-butyl methyl ether. The precipitate obtained from the filtrate was filtered off and washed with mother liquor. Both filter residues were taken up in 50 ml of ethyl acetate. The solution was concentrated on a rotary evaporator and the residue was dried under reduced pressure overnight. This gave 2.25 g of the target compound (95% pure, 64% of theory).

Workup

  1. filtrationthe precipitated solid was filtered off
  2. washthe filter residue was washed with 100 ml of water and twice with 20 ml of tert-butyl methyl ether
  3. customThe precipitate obtained from the filtrate
  4. filtrationwas filtered off
  5. washwashed with mother liquor
  6. concentrationThe solution was concentrated on a rotary evaporator
  7. customthe residue was dried under reduced pressure overnight

Sources & evidence

ORD record
ord-a4fffc52dce24e23b3ce7fe625f2cf43
Source dataset
uspto-grants-2014_07
Patent number
US08778964B2

Reaction notes

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