HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 4-(5-Bromo-pyridin-2-yl)-2-methyl-but-3-yn-2-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | 2-Methyl-3-butyn-2-ol | HCID 8258 | — |
| Reactant | 2,5-Dibromopyridine | HCID 69353 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-(5-Bromo-pyridin-2-yl)-2-methyl-but-3-yn-2-ol | HCID 22502471 | — |
Reaction Steps
Under an argon atmosphere 38 mg (0.2 mmol) CuI and 143 mg (0.2 mmol) Pd(PPh3)2Cl2 are added to a solution of 0.99 mL (10.0 mmol) 2-methyl-but-3-yn-2-ol and 2.44 g (10.0 mmol) 2,5-dibromo-pyridine in 50 mL THF and 2.8 mL (20 mmol) diisopropylamine and the reaction mixture is stirred for 15 min at RT. The reaction mixture is combined with water, exhaustively extracted with EtOAc and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, cyc/EtOAc 2:1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08618132B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-f84fc523022a4a0194b2398148db7467 |
| Source note | uspto-grants-2013_12 |