Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | HCID 58255771 | HCID 58255771 | — |
| Reactant | {6-Chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}boronic acid | HCID 86653303 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86653304 | HCID 86653304 | 29.9% |
Reaction Steps
6-Bromo-1-methyl-1H-indazol-4-amine (340 mg), sodium carbonate (638 mg) and Pd(dppf)Cl2 (110 mg) were weighed to a 10-20 ml microwave vial. {6-Chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}boronic acid (377 mg) dissolved in 1,4-dioxane (6 ml) was added followed by water (6 ml). The reaction was heated for 15 min at 120° C. in the microwave. The reaction was passed through a 2 g silica cartridge, washing with methanol. The solvent was evaporated under nitrogen blow down. The residue was purified on the ISCO companion using a 40 g silica cartridge and a gradient of 2-8% methanol in DCM (containing 1% ammonia) over 15 mins at 40 ml/min. Product-containing fractions were combined and dried down to give title compound (158 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08163743B2 |
|---|
| Source dataset | uspto-grants-2012_04 |
|---|
| ORD ID | ord-96256255827443ccadac58741674420a |
|---|
| Source note | uspto-grants-2012_04 |
|---|
