Sodium hydride → HCID 68154662, compound

HRID 1615761Notes

Reaction equation

HRID 1615761 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. 38 mg (0.86 mmol) sodium hydride were added to 0.30 g (0.76 mmol) tert-butyl 5-(3,5-difluorophenyl)-3-oxo-2-(tetrahydro-2H-pyran-4-yl)piperazine-1-carboxylate (isomer mixture 1) in 10 ml DMF. After 20 min, while cooling with an ice bath, 84 μl (0.86 mmol) methyl bromoacetate were added dropwise. 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-fad57f7d16d041c89510ff23f1825190
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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