HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → HCID 11575822, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (3-Chlorophenyl)boronic acid | HCID 2734323 | — |
| Reactant | benzoic acid N'-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-N'-isopropyl-hydrazide | HCID 58689907 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 11575822 | HCID 11575822 | 80.2% |
Reaction Steps
A solution of benzoic acid N′-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-N′-isopropyl-hydrazide (60 mg, 0.147 mmol) in DME (3 ml)/2M Na2CO3 (256 uL, 0.513 mmol) was treated with 3-chlorophenylboronic acid (34 mg, 0.219 mmol) and Pd[PPh3]4 (34 mg, 0.029 mmol) for 12 hours at 90° C. The reaction mixture was partitioned between water and ethyl acetate. 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 a white crystalline solid (52 mg, 80%). LC-MS m/e 441.24 (M+H+)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07317125B2 |
| Source dataset | uspto-grants-2008_01 |
| ORD ID | ord-ab07d94fad354539850c97d4ac7fb6ae |
| Source note | uspto-grants-2008_01 |