Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (3-Hydroxy-4-methylphenyl)boronic acid | HCID 4187664 | — |
| Reactant | 2-(5-Bromo-1-methylimidazol-4-yl)pyridine-4-carbonitrile | HCID 90408144 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 90407040 | HCID 90407040 | 69% |
Reaction Steps
To a microwave vessel was added 2-(5-bromo-1-methyl-1H-imidazol-4-yl)pyridine-4-carbonitrile (79 mg, 0.3 mmol), 3-hydroxy-4-methylphenyl boronic acid (55 mg, 0.36 mmol), PdCl2(dppf) (22 mg, 0.03 mmol), 2M Na2CO3 (0.3 mL, 0.6 mmol) in 2 mL dioxane. The reaction mixture was heated in a microwave oven at 120° C. for 1 hr. It was then purified by ISCO flash column (MeOH/DCM=0-5%) to give 60 mg product (69%). 1H NMR (400 MHz, DMSO-d6): δ 2.11 (3H, s), 3.46 (3H, s), 6.71 (1H, d, J=7.6 Hz), 6.75 (1H, s), 7.12 (1H, d, J=7.7 Hz), 7.52 (1H, d, J=4.9 Hz), 7.85 (1H, s), 8.06 (1H, s), 8.50 (1H, d, J=5 Hz), 9.36 (1H, s). [M+H] Calc'd for C17H14N4O, 291. Found, 291.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09133166B2 |
|---|
| Source dataset | uspto-grants-2015_09 |
|---|
| ORD ID | ord-33777049666444eb9ade7f6bf376ac7c |
|---|
| Source note | uspto-grants-2015_09 |
|---|
