HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 4-(2-methoxy-ethoxy)-benzoic acid N'-[2-(5-fluoro-2'-trifluoromethoxy-biphenyl-2-yloxy)-acetyl]-N'-isopropyl hydrazide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride) | HCID 2777204 | — |
| Reactant | 4-(2-methoxy-ethoxy)-benzoic acid N'-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-N'-isopropyl-hydrazide | HCID 58689919 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | 4-(2-methoxy-ethoxy)-benzoic acid N'-[2-(5-fluoro-2'-trifluoromethoxy-biphenyl-2-yloxy)-acetyl]-N'-isopropyl hydrazide | HCID 11721057 | 55% |
Reaction Steps
A solution of 4-(2-methoxy-ethoxy)-benzoic acid N′-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-N′-isopropyl-hydrazide (202 mg, 0.42 mmol) in DME (5 ml)/2M Na2CO3 (0.731 ml, 1.46 mmol) was with 2-trifluoromethoxyphenylboronic acid (129 mg, 0.63 mmol) and Pd[PPh3]4 (96.5 mg, 0.084 mmol) in a microwave oven at 150° C. for 10 min. 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 adsorbed on silica and purified on a silica gel column with a 45-60% ethyl acetate/hexane gradient to afford the product as a solid (129 mg, 55%). MS m/e 565.55 (M+H+)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07317125B2 |
| Source dataset | uspto-grants-2008_01 |
| ORD ID | ord-08141d7cd694409d874fffc6faaa056a |
| Source note | uspto-grants-2008_01 |