Allyl bromide → HCID 9967065, compound

HRID 558269Notes

Reaction equation

HRID 558269 reaction equation
[H-].[Na+].[CH2:3](Br)[CH:4]=[CH2:5].[Cl:7][C:8]1[CH:9]=[C:10]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[O:11][C:12]1[C:13]([CH2:19][CH3:20])=[N:14][NH:15][C:16]=1[CH2:17][CH3:18]>CN(C)C=O>[CH2:3]([N:14]1[C:13]([CH2:19][CH3:20])=[C:12]([O:11][C:10]2[CH:21]=[C:22]([Cl:24])[CH:23]=[C:8]([Cl:7])[CH:9]=2)[C:16]([CH2:17][CH3:18])=[N:15]1)[CH:4]=[CH2:5]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 9878953HCID 9878953, compound

Product 1

HCID 9967065HCID 9967065, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in oil, 770 mg, 19.2 mmol) was added to a stirred solution of allyl bromide (1.70 ml, 19.2 mmol) and the pyrazole of Example 3 (5.00 g, 17.5 mmol) in N,N-dimethylformamide (20 ml) at 0° C. under nitrogen. The reaction was warmed to room temperature and stirred for 1 hour. The reaction mixture was quenched by the addition of water (100 ml) and the aqueous phase was extracted with ether (2×50 ml). The combined organic phases were washed with water (30 ml) and brine (30 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure to leave a brown oil. The crude product was purified by flash column chromatography on silica gel eluting with pentane:ethyl acetate (80:20, by volume) to provide the title compound (5.00 g) as a yellow oil.

Workup

  1. customat 0° C.
  2. customThe reaction mixture was quenched by the addition of water (100 ml)
  3. extractionthe aqueous phase was extracted with ether (2×50 ml)
  4. washThe combined organic phases were washed with water (30 ml) and brine (30 ml)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto leave a brown oil
  9. customThe crude product was purified by flash column chromatography on silica gel eluting with pentane:ethyl acetate (80:20, by volume)

Sources & evidence

ORD record
ord-7767dbd7e3084f31a4343e1eabb48bfd
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

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