Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyrazole | HCID 1048 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 21949785 | HCID 21949785 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 21949919 | HCID 21949919 | 86.7% |
Reaction Steps
Pyrazole (23 mg, 0.330 mmol) was added in one portion to a stirred solution of the bromide of Example 137 (148 mg, 0.300 mmol) and sodium hydride (60% dispersion in oil, 13.2 mg, 0.330 mmol) in N,N-dimethylformamide (2 ml) at room temperature under nitrogen. The reaction was stirred for 5 hours, quenched with water (1.00 ml) and concentrated under reduced pressure. The residue was dissolved in dichloromethane (30 ml) and the resulting solution was washed with 1M aqueous potassium carbonate solution (10 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (98:2, by volume) to provide the title compound (125 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-a17fb76945874a95bf7d1bec6a04b273 |
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| Source note | uspto-grants-2011_11 |
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