Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Fluoropyridine | HCID 9746 | — |
| Reactant | 2-(Azetidin-3-yl)ethan-1-ol | HCID 19888391 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67294252 | HCID 67294252 | — |
Reaction Steps
2-(Azetidin-3-yl)ethanol (4.92 mmol, 0.498 g), 2-fluoropyridine (9.85 mmol, 0.846 ml, 0.956 g), triethylamine (14.77 mmol, 2.053 ml, 1.495 g) and methanol (2.5 ml) were combined and heated to 150° C. in a microwave for 40 minutes. TLC analysis showed some starting material remained and therefore the solution was heated for a further 40 minutes. The resulting solution was dissolved in DCM (c. 20 ml) and washed with water. Solvent was removed under reduced pressure to yield a crude product. This was then purified by flash chromatography (10 g silica column, DCM to 3% MeOH in DCM gradient). Appropriate fractions were combined and solvent removed under reduced pressure to give final product. 1H NMR (CDCl3) δ: 8.17 (d, 1H), 7.42 (t, 1H), 6.57 (t, 1H), 6.26 (d, 1H), 4.16 (t, 2H), 3.70 (m, 4H), 2.88 (m, 1H), 1.95 (q, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09115126B2 |
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| Source dataset | uspto-grants-2015_08 |
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| ORD ID | ord-d819ea22f3834c97af800a58fb039ca2 |
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| Source note | uspto-grants-2015_08 |
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