Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | 2-Methyl-3-butyn-2-ol | HCID 8258 | — |
| Reactant | 2-Amino-5-bromobenzenesulfonamide | HCID 820700 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 57751039 | HCID 57751039 | 46% |
Reaction Steps
2-Amino-5-bromobenzenesulfonamide (2 g, 7.96 mmol), copper(I) iodide (0.076 g, 0.40 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.280 g, 0.40 mmol) were slurried in anhydrous N,N-dimethylformamide (6 mL) in a microwave vial. 2-Methyl-3-butyn-2-ol (2.316 mL, 23.89 mmol) followed by diisopropylamine (3.37 mL, 23.89 mmol) were added, the vial was capped, purged with argon and the mixture was heated in a microwave at 100° C. for 30 min. The mixture was filtered and the solvent was evaporated in vacuo. Purification by column chromatography, using a gradient of 60-70% ethyl acetate in heptane as the eluent, gave 0.92 g (46% yield) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09145380B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-1ace700d37784a2ca8010e448c47cdf4 |
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| Source note | uspto-grants-2015_09 |
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