HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → HCID 54024436, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Acrylic Acid | HCID 6581 | — |
| Reactant | Tributylamine | HCID 7622 | — |
| Reactant | 2-Acetamido-5-bromopyridine | HCID 293097 | — |
| Catalyst | Triphenylphosphine | HCID 11776 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 54024436 | HCID 54024436 | 66.2% |
Reaction Steps
To a mixture of N-(5-bromo-pyridin-2-yl)-acetamide (1.26 g, 5.86 mmol) and tri-n-butylamine in xylenes (10 mL) is added Pd(OAc)2 (1.4 mg, 0.006 mmol) and triphenyl phosphine (15.4 mg, 0.06 mmol). Acrylic acid (0.48 mL, 7.03 mmol) is then added dropwise over 5 minutes. The mixture is heated to reflux for 5 hours. The solution is cooled to ambient temperatures. The mixture is diluted with water and the pH is adjusted to 4 with 1N HCl. The solution is extracted with EtOAc/CH2Cl2 (2:1). The resulting suspension is filtred to give the title compound (0.80 g, 3.88 mmol) as a white solid. MS (ion spray) 207, (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07612075B2 |
| Source dataset | uspto-grants-2009_11 |
| ORD ID | ord-1a0c07ab79f34b3d971b755b9288bfd3 |
| Source note | uspto-grants-2009_11 |