HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → HCID 11510518, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2,4-Difluorophenylboronic acid | HCID 2734334 | — |
| Reactant | benzoic acid N'-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-N'-isopropyl-hydrazide | HCID 58689907 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 11510518 | HCID 11510518 | 83.4% |
Reaction Steps
A solution of benzoic acid N′-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-N′-isopropyl-hydrazide (100 mg, 0.244 mmol) in DME (5 ml)/2M Na2CO3 (0.428 ml, 0.855 mmol) was treated with 2,4-difluorophenylboronic acid (77 mg, 0.489 mmol) and Pd[PPh3]4 (28 mg, 0.0244 mmol) at 90° C. overnight. The reaction mixture was partitioned between water and DCM. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 30-50% ethyl acetate/hexanes gradient to afford the product as solid (90 mg, 82%). MS m/e 443.38 (M+H+)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07317125B2 |
| Source dataset | uspto-grants-2008_01 |
| ORD ID | ord-9ca5a6b86a4446879451fbd814f9c39b |
| Source note | uspto-grants-2008_01 |