HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 3-methoxy-4-(1-methyl-1H-pyrazol-4-yl)aniline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Bromo-5-nitroanisole | HCID 101293 | — |
| Reactant | Diethyl (1-methyl-1H-pyrazol-4-yl)boronate | HCID 66709077 | — |
| Catalyst | Iron | HCID 23925 | — |
| Solvent | Ammonium chloride methanol | HCID 21190736 | — |
| Product | 3-methoxy-4-(1-methyl-1H-pyrazol-4-yl)aniline | HCID 58414472 | — |
Reaction Steps
A DMF solution of diethyl 1-methyl-1H-pyrazol-4-ylboronate, 4-bromo-3-methoxy nitrobenzene together with Pd(dppf) and K2CO3 were heated at reflux overnight. The product obtained was reduced with Fe in MeOH/ammonium chloride to provide the title compound. LC-MS (M+H)+=204.2. 1H NMR (400 MHz, DMSO-d6): δ ppm 7.84 (1H, s), 7.66 (1H, s), 7.19 (1H, J=8.2 Hz, d), 6.29 (1H, s), 6.18 (1H, J=2.0, 8.2 Hz, dd), 5.31 (2H, br s), 3.80 (3H, s), 3.75 (3H, s).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08486952B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-a0e15c5870e44026bc3438777036805a |
| Source note | uspto-grants-2013_07 |