Potassium Carbonate → ethyl 6-chloro-7-{[isopropyl(methyl)amino]methyl}-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 855045Notes

Reaction equation

HRID 855045 reaction equation
Br[CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:9]([C:13]([F:16])([F:15])[F:14])[O:10]2)=[CH:5][C:4]=1[Cl:22].[CH:23]([NH:26][CH3:27])([CH3:25])[CH3:24].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:22][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[CH2:2][N:26]([CH:23]([CH3:25])[CH3:24])[CH3:27])[O:10][CH:9]([C:13]([F:16])([F:15])[F:14])[C:8]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:7]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 78485N-MethylisopropylamineHCID 69517129ethyl 7-(bromomethyl)-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 69517159ethyl 6-chloro-7-{[isopropyl(methyl)amino]methyl}-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The ethyl 7-(bromomethyl)-6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate from Example 16, Step 3 (01597/1 PR) (1.0 g, 2.5 mmol) was dissolved in DMF (5 mL). The solution was cooled at ice bath under nitrogen and the isopropyl(methyl)-amine (0.26 mL, 2.5 mmole) was added into the solution followed by addition of potassium carbonate (0.345 g, 2.5 mmol). After the mixture was stirred at r.t for 3 hr, LCMS indicated that the product was formed. The reaction was quenched with water and extracted with EtOAc. The organic layer was washed with brine and dried over MgSO4 and filtered. The filtrate was concentrated to afford the crude product. The ester was of suitable purity to use without further purification.

Workup

  1. temperatureThe solution was cooled at ice bath under nitrogen
  2. customwas formed
  3. customThe reaction was quenched with water
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-39167f5f7ad844f3961b04a2e95b5f93
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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