Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 1-Decyne | HCID 12997 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 3-Bromo-5-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-pyridine | HCID 11288721 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 54273284 | HCID 54273284 | 85% |
Reaction Steps
To a solution of 5-bromo-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)-pyridine (544 mg, 2.00 mmol), bis(triphenylphosphine)palladium(II) chloride (28 mg, 0.038 mmol) and copper (I) iodide (5 mg, 0.038 mmol) in CH2Cl2 (3.0 mL) and NEt3 (1.0 mL) was added 1-decyne (0.553 mL, 3.00 mmol). The mixture was refluxed overnight then cooled to room temperature. Water (2 mL) was added, and solid sodium bicarbonate was added until the aqueous layer was saturated. The mixture was extracted with EtOAc, which was dried over MgSO4, filtered and concentrated. The residue was chromatographed on a silica gel column, eluting with NH4OH/MeOH/EtOAc 0:1:9 and 1:10:90 to afford an oil (543 mg, 85%). MS (CI/NH3) m/z 329 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ 0.90 (t, J=6.9 Hz, 3H), 1.23-2.10 (m, 14H), 2.25-2.41 (m, 1H), 2.41 (t, J=7.3 Hz, 2H), 2.50 (s, 3H), 2.60-2.75 (m, 1H), 3.08-3.21 (m, 1H),, 3.89-4.06 (m, 2H), 7.19 (s, 1H), 8.15-8.28 (m, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06127386 |
|---|
| Source dataset | uspto-grants-2000_10 |
|---|
| ORD ID | ord-11e97aa9f0b649f783856a87c6d415b2 |
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| Source note | uspto-grants-2000_10 |
|---|
