Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | (2-Bromoethoxy)-tert-butyldimethylsilane | HCID 3608067 | — |
| Reactant | HCID 9943260 | HCID 9943260 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66707677 | HCID 66707677 | 15.2% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08063044B2 |
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| Source dataset | uspto-grants-2011_11 |
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| ORD ID | ord-9f1ad3d6f744456aaa92f7f7e05118b7 |
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| Source note | uspto-grants-2011_11 |
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