Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Bromomethyl 2-methoxyphenyl ketone | HCID 123440 | — |
| Reactant | 2-Amino-5-bromo-3-methylpyridine | HCID 137934 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 59843198 | HCID 59843198 | 54.2% |
Reaction Steps
A mixture of 2-bromo-2′-methoxyacetophenone (0.500 g, 2.183 mmol) and 2-amino-5-bromo-3-methylpyridine (0.408 g, 2.183 mmol) in ethanol (8 mL) was heated to 80° C. for 16 hours in a pressure vessel. A yellow thick precipitate formed. Water was added and the solid was extracted with ethyl acetate (some DCM and MeOH were added to help in the dissolution). The organic extracts were then washed with brine, dried over Na2SO4, filtered and concentrated and the residue was purified by silica gel chromatography (Biotage SNAP 100 g, 10 to 20% ethyl acetate in hexanes) to give 220 (0.375 g, 1.182 mmol, 54.2% yield) as a white solid. LRMS (ESI): calc. 316.02 found 317.1 (MH)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08338437B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-131aaa0041c0475f9ee6cf44eb798276 |
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| Source note | uspto-grants-2012_12 |
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