HuagongsheHuagongshe Chemistry Print Report · For research reference only
Morpholine → (6-Bromopyridin-3-YL)(morpholino)methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 6-Bromonicotinic acid | HCID 238932 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (6-Bromopyridin-3-YL)(morpholino)methanone | HCID 65809001 | 79% |
Reaction Steps
The mixture of 6-bromonicotinic acid (700 mg, 3.5 mmol), morpholine (391 mg, 4.5 mmol), HATU (220 mg, 0.59 mmol) and DIPEA (0.3 mL) in 10 mL of dry THF was stirred at room temperature for 14 hours. The reaction solution was evaporated to dryness. To the residue was added 20 mL of 0.5N hydrochloride, and the mixture was extracted with ethyl acetate (50 mL×3). The organic layer was dried over sodium sulfate and concentrated to give (6-bromopyridin-3-yl)(morpholino)methanone (750 mg, 79%). LC-MS: 271, 273 [M+H]+, tR=1.290 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08742098B2 |
| Source dataset | uspto-grants-2014_06 |
| ORD ID | ord-9d71cb354a264a729e5186fd6e9343ee |
| Source note | uspto-grants-2014_06 |