Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | 2,6-Difluorobenzoyl chloride | HCID 87438 | — |
| Reactant | 6-Bromo-4-methylpyridin-3-amine | HCID 19926094 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 118021299 | HCID 118021299 | 70.2% |
Reaction Steps
To a (0° C.) cooled and stirred solution of 2,6-difluorobenzoyl chloride (357 μL, 2.83 mmol) in DCM (5 mL) was added 6-bromo-4-methylpyridin-3-amine (583 mg, 3.12 mmol) followed by the addition of pyridine (344 μL, 4.25 mmol). The resulting mixture was then stirred at room temperature overnight. Water (5 mL) was added to the above mixture and then extracted with DCM (3×10 mL). The combined organic layers were washed with 10% aq.HCl (10 mL), dried (Na2SO4) and filtered. The filtrate was concentrated under vacuum to afford 650 mg (70%) of the title compound as a white solid. 1HNMR (400 MHz, DMSO-d6) δ 10.56 (s, 1H, D2O exchangeable), 8.41 (s, 1H), 7.66 (s, 1H), 7.65-7.58 (m, 1H), 7.27 (t, J=7.0 Hz, 2H), 2.27 (m, 3H); (ESI-MS (m/z) 327, 329 [(MH)+, Br79, 81].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09399638B2 |
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| Source dataset | uspto-grants-2016_07 |
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| ORD ID | ord-45472d6bd3874fa18fe40c9ead3b253a |
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| Source note | uspto-grants-2016_07 |
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