HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 5-Amino-4-cyano-3-(2'methylsulfanyl-biphenyl-4-yl)-thiophene-2-carboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-(Methylthio)benzeneboronic acid | HCID 2773543 | — |
| Reactant | 5-Amino-4-cyano-3-(4-iodo-phenyl)-thiophene-2-carboxylic acid ethyl ester | HCID 68521862 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 5-Amino-4-cyano-3-(2'methylsulfanyl-biphenyl-4-yl)-thiophene-2-carboxylic acid ethyl ester | HCID 68524048 | — |
Reaction Steps
Combine 5-amino-4-cyano-3-(4-iodo-phenyl)-thiophene-2-carboxylic acid ethyl ester (0.829 mmol) in dioxane and add 2-(methylthio)phenylboronic acid, tetrakis(triphenylphosphine)palladium (0), and 1.4 ml of 2M sodium carbonate solution and heat to reflux. After 3 hours, purification by radial chromatography (6000 micron Si plate) eluting with 10-20% ethylacetate/methylene chloride provides the title compound: 1H NMR (400 MHz, CDCl3) δ 7.49-7.19 (m, 8H), 5.26 (s, 2H), 4.17 (q, 2H, J=7.2 Hz), 2.38 (s, 3H), 1.18 (t, 3H, J=7.0 Hz), MS found (M+1) 395.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07642361B2 |
| Source dataset | uspto-grants-2010_01 |
| ORD ID | ord-30fc145f6fd74b86a7292c9102f70c46 |
| Source note | uspto-grants-2010_01 |