Sodium hydride → HCID 66707677, compound

HRID 558308Notes

Reaction equation

HRID 558308 reaction equation
[H-].[Na+].Br[CH2:4][CH2:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].[CH:14]([C:17]1[C:21]([O:22][C:23]2[CH:24]=[C:25]([C:31]#[N:32])[CH:26]=[C:27]([CH:30]=2)[C:28]#[N:29])=[C:20]([CH3:33])[NH:19][N:18]=1)([CH3:16])[CH3:15]>CN(C)C=O>[Si:7]([O:6][CH2:5][CH2:4][N:19]1[C:20]([CH3:33])=[C:21]([O:22][C:23]2[CH:24]=[C:25]([C:31]#[N:32])[CH:26]=[C:27]([CH:30]=2)[C:28]#[N:29])[C:17]([CH:14]([CH3:16])[CH3:15])=[N:18]1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 9943260HCID 9943260, compound

Product 1

HCID 66707677HCID 66707677, compoundYield 15.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in oil, 45 mg, 1.12 mmol) was added to a stirred solution of 2-bromoethoxy-t-butyldimethylsilane (270 mg, 1.12 mmol) and the pyrazole of Example 95 (250 mg, 0.930 mmol) in N,N-dimethylformamide (5 ml) at 0° C. under nitrogen. The reaction was warmed to room temperature and stirred for 12 hours. The reaction mixture was quenched by the addition of water (50 ml) and the aqueous phase was extracted with ethyl acetate (3×30 ml). The combined organic phases were 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 pentane:ethyl acetate (80:20, by volume) to provide the title compound (60 mg) as a colourless oil.

Workup

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

Sources & evidence

ORD record
ord-9f1ad3d6f744456aaa92f7f7e05118b7
Source dataset
uspto-grants-2011_11
Patent number
US08063044B2

Reaction notes

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