Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Octyne | HCID 12370 | — |
| Reactant | (S)-Tert-butyl 2-(((5-bromopyridin-3-YL)oxy)methyl)azetidine-1-carboxylate | HCID 10688713 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Sodium Hydroxide | HCID 14798 | — |
| Product | HCID 69830940 | HCID 69830940 | 452.2% |
Reaction Steps
To a solution of 5-bromo-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine from step 54b (450 mg, 1.3 mmol) in 10 mL of CH2Cl2 was added triethylamine (0.6 mL), Pd(PPh3)2Cl2 (25 mg), CuI (a catalytic amount) and 1-octyne (0.37 mL, 0.26 mmol). The reaction mixture was heated at reflux for 40 hours. The mixture was diluted with CH2Cl2, and 2 mL of 10% NaOH were added. The organic layer was separated and dried, and the solvent was removed under reduced pressure. The residue was purified by chromatography, eluting with 1 to 2% MeOH in CH2Cl2 to afford the title compound (438 mg). MS (CI/NH3) m/z 373 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ 0.91 (m, 3H), 1.32 (m, 2H), 1.41 (s, 9H), 1.44 (m, 2H), 1.61 (m, 2H), 2.30 (m, 2H), 2.41 (m, 2H), 3.88 (m, 2H), 4.11 (m, 1H), 4.30 (m, 1H), 4.50 (m, 1H), 7.23 (m, 1H), 8.23 (br s, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06437138B1 |
|---|
| Source dataset | uspto-grants-2002_08 |
|---|
| ORD ID | ord-77b2089acc03439181f991936e65cce4 |
|---|
| Source note | uspto-grants-2002_08 |
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