Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Thiopheneboronic acid | HCID 2733960 | — |
| Reactant | 2'-amino-6-bromo-1'-methyl-2-phenylspiro[chroman-4,4'-imidazol]-5'(1'H)-one | HCID 58423768 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 58424774 | HCID 58424774 | 4.5% |
Reaction Steps
A mixture of 2′-amino-6-bromo-1′-methyl-2-phenylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (21 mg, 0.05 mmol), thiophen-2-ylboronic acid (14 mg, 0.1 mmol), Cs2CO3 solution (2 M, 0.5 mL) and Pd(PPh3)2Cl2 (10 mg) in 1,4-dioxane (1 mL) was stirred in a microwave test tube under Ar at 120° C. for 35 minutes. The reaction mixture was concentrated in vacuo to give the residue, which was purified by preparative TLC to give 2′-amino-1′-methyl-2-phenyl-6-(thiophen-2-yl)spiro[chroman-4,4′-imidazol]-5′-(1′H)-one (0.87 mg, 4%). 1H-NMR (MeOD): 2.45-2.54 (M, 1H), 2.60-2.63 (m, 1H), 3.32 (s, 3H), 5.88 (d, 1H), 7.06-7.14 (m, 2H), 7.33-7.39 (m, 2H), 7.41-7.50 (m, 3H), 7.51-7.64 (m, 4H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08450308B2 |
|---|
| Source dataset | uspto-grants-2013_05 |
|---|
| ORD ID | ord-8c77dcd5ed1d4838970de4a830161ad1 |
|---|
| Source note | uspto-grants-2013_05 |
|---|