HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 3-Fluoro-4-(morpholine-4-carbonyl)phenylboronic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | 4-Carboxy-3-fluorophenylboronic acid | HCID 2763201 | — |
| 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 | Dimethylformamide | HCID 6228 | — |
| Product | 3-Fluoro-4-(morpholine-4-carbonyl)phenylboronic acid | HCID 57618415 | 87.3% |
Reaction Steps
To a solution of 4-borono-2-fluorobenzoic acid (1.0 g, 5.43 mmol) and HATU (2.0 g, 5.43 mmol) in DMF (20.0 mL) was added morpholine (0.9 g, 10.87 mmol) at room temperature. The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was poured into ice cold water, acidified with 1N HCl, extracted with EtOAc (2×50 mL). The organic layer was washed with brine solution (20 mL), dried over anhydrous Na2SO4 and solvent was evaporated under reduced pressure to afford 1.2 g of crude compound as a colourless gum. Crude compound was directly used for the next step without any further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09321748B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-cebe5f0af8654e32bfbe31811e2ffc75 |
| Source note | uspto-grants-2016_04 |