Allyl bromide → HCID 25184912, compound

HRID 1878090Notes

Reaction equation

HRID 1878090 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]([OH:14])[C:11]([CH2:15][CH3:16])=[C:10]([CH3:17])[N:9]=2)=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH2:24](Br)[CH:25]=[CH2:26]>CN(C=O)C>[CH2:26]([O:14][C:12]1[C:11]([CH2:15][CH3:16])=[C:10]([CH3:17])[N:9]=[C:8]([C:5]2[N:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)[N:13]=1)[CH:25]=[CH2:24]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 178436787HCID 178436787, compound

Product 1

HCID 25184912HCID 25184912, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of compound of example 52 (0.200 g, 0.86 mmol) in DMF (3 mL), was added K2CO3 (0.18 g, 1.302 mmol) and stirred at 25° C. for 10 minutes, followed by slow addition of allyl bromide (0.15 g, 1.302 mmol). The reaction mixture was stirred at 25° C. for 1 hour. DMF was removed under vacuum, and the reaction mass was quenched by water, extracted with ethyl acetate (3×20 mL), dried over sodium sulfate and concentrated to obtain the crude product, which was taken for synthesis of compound of example 64 without purification and characterization.

Workup

  1. stirringThe reaction mixture was stirred at 25° C. for 1 hour
  2. customDMF was removed under vacuum
  3. customthe reaction mass was quenched by water
  4. extractionextracted with ethyl acetate (3×20 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c6a2e93cb51246fc859dfaec6e9c6c49
Source dataset
uspto-grants-2012_11
Patent number
US08314103B2

Reaction notes

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