HuagongsheHuagongshe Chemistry Print Report · For research reference only
Nitrogen → 4'-Formyl-3-biphenylcarboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-Bromobenzaldehyde | HCID 70741 | — |
| Reactant | (3-Carbamoylphenyl)boronic acid | HCID 2737814 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | 4'-Formyl-3-biphenylcarboxamide | HCID 59316529 | — |
Reaction Steps
A mixture of 4-bromobenzaldehyde (2.78 g; 15.0 mmol), [3-(aminocarbonyl)-phenyl]boronic acid (2.72 g; 16.5 mmol), PdCl2(dppf).CH2Cl2 (0.306 g; 0.38 mmol), DME (25 mL) and Na2CO3 (25 mL of a 2M solution) was sparged 20 min with N2 and heated under reflux for 90 min (consumption of aryl bromide observed by LC/MS). Upon cooling, the mixture was partitioned between EtOAc/H2O, layers were separated, and the aqueous layer was extracted with EtOAc (×2). Combined organics were washed (H2O, brine), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a tan solid. LC/MS (method A) 1.91 min, m/z 226 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08822518B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-f16869d2600a431382fa4e227ab303ab |
| Source note | uspto-grants-2014_09 |