Cesium carbonate → HCID 17975832, compound

HRID 2108853Notes

Reaction equation

HRID 2108853 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:12]=[C:11]2[C:6]([C:7]([OH:13])=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]1[C:30](=[O:37])[CH:31]=[C:32]([CH2:35][OH:36])[O:33][CH:34]=1>CN(C=O)C>[F:15][C:2]([F:1])([F:14])[C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:13][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]3[C:30](=[O:37])[CH:31]=[C:32]([CH2:35][OH:36])[O:33][CH:34]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 179758375-(5-Bromopentyloxy)-2-(hydroxymethyl)-4H-pyran-4-oneHCID 178516425HCID 178516425, compound

Product 1

HCID 17975832HCID 17975832, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
75 °C

Procedure

7-Trifluoromethyl-4-quinolinol (320 mg, 1.5 mmol), Cs2CO3 (500 mg, 1.5 mmol) and anhydrous DMF (3 mL) were stirred at 70° C. in a 50 ml round-bottomed flask equipped with a magnetic stirrer. After 20 min, 5-(5-bromopentyloxy)-2-(hydroxymethyl)-4H-pyran-4-one 10 (420 mg, 1.4 mmol) in DMF (2 mL) was added and the reaction mixture was stirred for 15 h at 75° C. DMF was evaporated at 60° C. and the reaction mixture was poured in 20 mL of H2O and extracted with EtOAc (3×100 mL). The organic layer was washed with brine (10 mL), dried over MgSO4, filtered and evaporated to dryness. The crude compound was purified by column chromatography (SiO2; CH2Cl2:MeOH=98:2 to 90:10) to give after evaporation 5-(5-(7-(trifluoromethyl)quinolin-4-yloxy)pentyloxy)-2-(hydroxymethyl)-4H-pyran-4-one 12 (300 mg, 47% yield) as a white solid.

Workup

  1. customequipped with a magnetic stirrer
  2. customDMF was evaporated at 60° C.
  3. additionthe reaction mixture was poured in 20 mL of H2O
  4. extractionextracted with EtOAc (3×100 mL)
  5. washThe organic layer was washed with brine (10 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe crude compound was purified by column chromatography (SiO2; CH2Cl2:MeOH=98:2 to 90:10)
  10. customto give

Sources & evidence

ORD record
ord-84c1840a2ab34905b1dcd79c11dac3cf
Source dataset
uspto-grants-2009_04
Patent number
US07514432B2

Reaction notes

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