Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(tert-Butoxycarbonylaminomethyl)phenylboronic acid | HCID 3863163 | — |
| Reactant | HCID 58495549 | HCID 58495549 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 58495669 | HCID 58495669 | 64.1% |
Reaction Steps
To a solution of 2-bromo-5-(3,3-dimethylbutyryl)-thiophene (187 mg, 0.7 mmol) in dioxane (7 mL) add a solution of aqueous 2M Na2CO3 (0.9 mL), [4-(N-tert-butoxycarbonyl-aminomethyl)phenyl]boronic acid (216 mg, 0.8 mmol) and tetrakis(triphenylphosphine)-palladium(0) (41 mg, 0.03 mmol). Heat the mixture at 90° C. overnight. Cool at room temperature, add water and extract with EtOAc. Dry the organic phase over MgSO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane/EtOAc (4:1) to obtain the desired intermediate (174 mg, 63%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08680091B2 |
|---|
| Source dataset | uspto-grants-2014_03 |
|---|
| ORD ID | ord-07b9f9e2d4af44a7b6340308d0f226fb |
|---|
| Source note | uspto-grants-2014_03 |
|---|
