Allyl bromide → HCID 25184847, compound

HRID 1878084Notes

Reaction equation

HRID 1878084 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]([OH:14])[CH:11]=[C:10]([C:15]([F:18])([F:17])[F:16])[N:9]=2)=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH2:25](Br)[CH:26]=[CH2:27]>CN(C=O)C>[CH2:27]([O:14][C:12]1[CH:11]=[C:10]([C:15]([F:18])([F:17])[F: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:26]=[CH2:25]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 178507455HCID 178507455, compound

Product 1

HCID 25184847HCID 25184847, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of compound of example 15 (0.200 g, 0.78 mmol) in DMF (3 mL), was added K2CO3 (0.162 g, 1.170 mmol) and the mixture was stirred at 25° C. for 10 minutes, followed by slow addition of allyl bromide (0.14 g, 1.17 mmol). The reaction mixture was stirred at 25° C. for 45 minutes. 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 5% methanol in chloroform as an eluent to obtain the title compound.

Workup

  1. stirringThe reaction mixture was stirred at 25° C. for 45 minutes
  2. customDMF was removed under vacuum
  3. customthe reaction mass quenched by water
  4. extractionextracted with ethyl acetate (3×20 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto obtain the crude product, which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-677bf842a7474d88bdfa4e8d853d5e4b
Source dataset
uspto-grants-2012_11
Patent number
US08314103B2

Reaction notes

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