Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 4-Methoxyphenol | HCID 9015 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | (1-chloro-isoquinolin-3-yl)-(5-methyl-1H-pyrazol-3-yl)-amine | HCID 57799635 | — |
| Solvent | Dimethyl Ether | HCID 8254 | — |
| Product | HCID 57799809 | HCID 57799809 | 22.4% |
Reaction Steps
NaH (155 mg) was added to a solution of 4-methoxy-phenol (500 mg) in dimethyl ether (DME) (2 ml) and stirred for 1 hour. (1-chloro-isoquinolin-3-yl)-(5-methyl-1H-pyrazol-3-yl)-amine (100 mg) was added to the mixture, and the mixture was heated at 150° C. for 30 minutes under microwave irradiation. The reaction mixture was acidified to pH=7 with acetic acid and purified by preparative LC-MS to give [1-(4-methoxy-phenoxy)-isoquinolin-3-yl]-(5-methyl-1H-pyrazol-3-yl)-amine (30 mg). LC-MS: m/e 347(MH+). 1H NMR(CDCl3): δ 2.18(s, 3H), δ 3.85(s, 3H), δ 5.64(s, 1H), δ 6.78(s, 1H), δ 6.87(s, 1H), δ 7.02(m, 2H), δ 7.21(m, 3H), δ 7.31(m, 1H), δ 7.54(d, 2H), δ 8.27(d, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07572809B2 |
|---|
| Source dataset | uspto-grants-2009_08 |
|---|
| ORD ID | ord-29eac341777a465f8a0909eed06d3638 |
|---|
| Source note | uspto-grants-2009_08 |
|---|