Sodium hydride → HCID 68154662, compound

HRID 1615762Notes

Reaction equation

HRID 1615762 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH:11]2[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:14]([CH:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[C:13](=[O:30])[NH:12]2)[CH:7]=[C:8]([F:10])[CH:9]=1.Br[CH2:32][C:33]([O:35][CH3:36])=[O:34]>CN(C=O)C>[F:3][C:4]1[CH:5]=[C:6]([CH:11]2[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:14]([CH:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[C:13](=[O:30])[N:12]2[CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH:7]=[C:8]([F:10])[CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 68154447HCID 68154447, compound2×

Product 1

HCID 68154662HCID 68154662, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At 0° C. 0.16 g (3.7 mmol) sodium hydride was added to 1.30 g (3.3 mmol) tert-butyl 5-(3,5-difluorophenyl)-3-oxo-2-(tetrahydro-2H-pyran-4-yl)piperazine-1-carboxylate (isomer mixture 2) in 20 ml DMF. After 20 min 0.36 ml (3.7 mmol) methyl bromoacetate were added dropwise while cooling with an ice bath. Then the mixture was stirred for 30 min in the ice bath and for 5 h at RT. The reaction mixture was poured onto water and extracted with ethyl acetate. The organic phase was washed with water, dried and evaporated down.

Workup

  1. customAt 0° C
  2. temperaturewhile cooling with an ice bath
  3. additionThe reaction mixture was poured onto water
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with water
  6. customdried
  7. customevaporated down

Sources & evidence

ORD record
ord-ac31e6a53e734c21bddb0a0b71ae27c8
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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