Sodium hydride → HCID 57516747, compound

HRID 1917551Notes

Reaction equation

HRID 1917551 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:15])[C:10]([CH3:14])([CH3:13])[CH2:11]Cl)=[N:6][CH:7]=1.[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:11][C:10]([CH3:14])([CH3:13])[C:9]2=[O:15])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 57516746HCID 57516746, compound

Product 1

HCID 57516747HCID 57516747, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

(250 mg, 0.738 mmol) N-(5-Bromo-pyridin-2-yl)-3-chloro-2,2-dimethyl-propionamide (Example 97, step 1) dissolved in DMF (3 ml) was added at room temperature to a solution of NaH (29.5 mg, 0.738 mmol, 1 equiv.) in 5 ml DMF. The mixture was stirred for 3 hours at 70° C. The reaction mixture was evaporated and the crude product was purified by flash chromatography on silica gel column and eluting with an ethyl acetate:heptane gradient 10:90 to 15:85. The desired 1-(5-bromo-pyridin-2-yl)-3,3-dimethyl-azetidin-2-one (160 mg, 72% yield) was obtained as a white solid.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe crude product was purified by flash chromatography on silica gel column
  3. washeluting with an ethyl acetate

Sources & evidence

ORD record
ord-32e58ac62b99485d9b3fd379c9679c2c
Source dataset
uspto-grants-2013_12
Patent number
US08618296B2

Reaction notes

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