Water → HCID 58136578, compound

HRID 877247Notes

Reaction equation

HRID 877247 reaction equation
[H-].[Na+].[F:3][C:4]([F:13])([F:12])[C:5]1[CH:6]=[CH:7][C:8](=[O:11])[NH:9][CH:10]=1.Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([CH:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:18][CH:17]=1.O>CN(C=O)C.C(OCC)(=O)C>[CH:30]1([CH:22]([C:19]2[CH:20]=[CH:21][C:16]([CH2:15][N:9]3[CH:10]=[C:5]([C:4]([F:3])([F:12])[F:13])[CH:6]=[CH:7][C:8]3=[O:11])=[CH:17][CH:18]=2)[C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1474432-Hydroxy-5-(trifluoromethyl)pyridineHCID 15225592tert-Butyl 2-(4-(bromomethyl)phenyl)-2-cyclopentylacetate

Product 1

HCID 58136578HCID 58136578, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

73.6 mg (1.84 mmol, 60% pure) of sodium hydride were added to 300 mg (1.84 mmol) of 5-(trifluoromethyl)pyridin-2(1H)-one in 2.5 ml of DMF. After 30 min of stirring, 500 mg (1.42 mmol) of tert-butyl(+/−)-[4-(bromomethyl)phenyl](cyclopentyl)acetate were added. After a further 2 h of stirring at RT, the reaction mixture was warmed to 40° C. for 1 h. Water and ethyl acetate were then added to the mixture, and the phases were separated. The organic phase was washed with saturated sodium chloride solution and dried over magnesium sulfate. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 6:1 to 4:1). This gave 522.0 mg (84.7% of theory) of the target compound.

Workup

  1. stirringAfter a further 2 h of stirring at RT
  2. customthe phases were separated
  3. washThe organic phase was washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 6:1 to 4:1)

Sources & evidence

ORD record
ord-85d52b59be174ec79ee38c1bf9e2c9a9
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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