Allyl bromide → HCID 25184908, compound

HRID 1878082Notes

Reaction equation

HRID 1878082 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]([OH:14])[C:11]([Cl:15])=[C:10]([CH3:16])[N:9]=2)=[N:6][CH:7]=1.[H-].[Na+].[CH2:19](Br)[CH:20]=[CH2:21]>CN(C=O)C>[CH2:21]([O:14][C:12]1[C:11]([Cl:15])=[C:10]([CH3:16])[N:9]=[C:8]([C:5]2[N:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)[N:13]=1)[CH:20]=[CH2:19]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 178432548HCID 178432548, compound

Product 1

HCID 25184908HCID 25184908, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of compound of example 16 (0.275 g, 1.1620 mmol) in DMF (3 mL) at 0° C., was added NaH (0.046 g, 1.1620 mmol) and allyl bromide (0.14 g, 1016 mmol) slowly and the reaction mixture was stirred at 25° C. for 4 hours. DMF was removed under vacuum, and the reaction mass quenched by water, extracted with ethyl acetate (3×20 mL), dried over sodium sulfate and concentrated to obtain the crude product, which was purified by column chromatography using silica gel and 8% methanol in chloroform as an eluent to obtain the title compound.

Workup

  1. customDMF was removed under vacuum
  2. customthe reaction mass quenched by water
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto obtain the crude product, which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-f36bc549420b44209a6ea30e1d0f1ded
Source dataset
uspto-grants-2012_11
Patent number
US08314103B2

Reaction notes

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