HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dibromomethane → 2-Bromo-4-methyl-5-[[2-(1-methyl-1H-pyrazol-4-yl)-4-pyridinyl]oxy]pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dibromomethane | HCID 3024 | — |
| Reactant | Tert-Butyl nitrite | HCID 10906 | — |
| Reactant | 4-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-amine | HCID 68664096 | — |
| Catalyst | Tetrabutylammonium Bromide | HCID 74236 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 2-Bromo-4-methyl-5-[[2-(1-methyl-1H-pyrazol-4-yl)-4-pyridinyl]oxy]pyridine | HCID 90416626 | 86% |
Reaction Steps
A solution of Example A2 (0.2 g, 0.71 mmol) in dibromomethane (5 mL) was treated with tetrabutylammonium bromide (0.92 g, 2.84 mmol) and t-butylnitrite (0.7 g, 7.11 mmol) and stirred at RT for 4 h. The mixture was diluted with EtOAc, washed successively with satd. NaHCO3, water, and brine, dried over Na2SO4 and concentrated to dryness to afford 2-bromo-4-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridine as off-white solid (0.21 g, 86%). MS (ESI) m/z: 345.1 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09181223B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-c5132f48ad7c4743a69060e34182d8a4 |
| Source note | uspto-grants-2015_11 |