HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → (3-Tert-butoxycarbonylamino-2'-methanesulfonyl-biphenyl-4-yl)-carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-(Methylsulfonyl)phenylboronic Acid | HCID 2773539 | — |
| Reactant | 1,2-Di(tert-Butyloxycarbonylamino)-4-bromobenzene | HCID 13007803 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | (3-Tert-butoxycarbonylamino-2'-methanesulfonyl-biphenyl-4-yl)-carbamic acid tert-butyl ester | HCID 57935002 | 86% |
Reaction Steps
A mixture of (5-bromo-2-tert-butoxycarbonylamino-phenyl)-carbamic acid tert-butyl ester (Example 1, Step A, 8.81 g, 0.0385 mol), 2-methylsulfonylphenylboronic acid (10.00 g, 0.0500 mol), Pd(dppf)Cl2.CH2Cl2 (4.71 g, 0.0578 mmol), and Na2CO3 (24.46 g, 0.116 mol) in 1,2-dimethoxyethane (200 mL) and water (50 mL) was heated 80° C. for 12 hours under inert atmosphere. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by chromatography (silica, EtOAc: hexanes, 1:2) to afford the title compound as a yellow oil (15.30 g, 86%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07612211B2 |
| Source dataset | uspto-grants-2009_11 |
| ORD ID | ord-645fa1f850754c7f897fb80305295720 |
| Source note | uspto-grants-2009_11 |