HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phenylacetylene → 1-Isobutyl-6-phenylethynyl-1H-benzimidazol-2-ylamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phenylacetylene | HCID 10821 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Tris(1,1-dimethylethyl)phosphine | HCID 83681 | — |
| Reactant | 1-Isobutyl-2-amino-6-bromobenzimidazole | HCID 65346776 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 1-Isobutyl-6-phenylethynyl-1H-benzimidazol-2-ylamine | HCID 66869277 | 60.8% |
Reaction Steps
Heat a mixture of Pd(OAc)2 (1.25 g, 5.59 mmol), CuI (0.42 g, 2.23 mmol), P(t-Bu)3 (2.76 mL, 11.2 mmol), K2CO3 (30.3 g, 223.8 mmol) and 6-bromo-1-isobutyl-1H-benzimidazol-2-ylamine (30 g, 111.9 mmol) in DMSO (200 mL) at 70° C. Add phenylacetylene (14.6 mL, 133.4 mmol) and heat the mixture for 6 hours at 70° C. Cool and dilute with H20. Filter the residue through a pad of celite. Recrystallize the crude mixture in toluene to give the desired compound as a white solid (19.68 g, 60%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07863310B2 |
| Source dataset | uspto-grants-2011_01 |
| ORD ID | ord-2f72b2442ebc437294069a615fa846b4 |
| Source note | uspto-grants-2011_01 |