Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 1-(2-Hydroxyethyl)pyrrole | HCID 10975438 | — |
| Reactant | HCID 56941887 | HCID 56941887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66802256 | HCID 66802256 | 53% |
Reaction Steps
A mixture of 2-pyrrol-1-yl-ethanol (17 mg, 0.15 mmol) and NaH (5 mg, 60% dispersion in mineral oil, 0.13 mmol) in THF (200 μL) was stirred at 0° C. for 15 min. A solution of methyl 3-{[(5-chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoate (Example 74) (20 mg, 0.05 mmol) in THF (100 μL) was added, and the reaction mixture was stirred at 0° C. for another 6 h. The reaction was quenched by addition of cold MeOH and 4:1 water/HOAc (50 μL) before purified by preparative HPLC. The title compound was obtained in 53% yield (12.5 mg). MS (ESI+) m/z 475 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09233946B2 |
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| Source dataset | uspto-grants-2016_01 |
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| ORD ID | ord-2dd04b8e3fa54703afec9d7644faa876 |
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| Source note | uspto-grants-2016_01 |
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