Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | (S)-1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propan-2-ol | HCID 67050610 | — |
| Reactant | 6-(2,6-dichloro-3,5-dimethoxyphenyl)-3-iodo-1H-pyrazolo[4,3-c]pyridine | HCID 178493454 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 76284887 | HCID 76284887 | 16.9% |
Reaction Steps
A mixture of 6-(2,6-dichloro-3,5-dimethoxyphenyl)-3-iodo-1H-pyrazolo[4,3-c]pyridine (15 mg, 0.033 mmol) (Example 28, Step 4), (2S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-2-ol (10 mg, 0.04 mmol), [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) complexed with dichloromethane (1:1) (2 mg, 0.003 mmol), and potassium phosphate (14 mg, 0.067 mmol) in 1,4-dioxane (0.3 mL) and water (0.05 mL) in a reaction vial was degassed and sealed. It was stirred at 90° C. overnight. After cooling it was diluted with methanol, purified by RP-HPLC (pH=2) to afford the desired product (2.5 mg) as TFA salt. LCMS (M+H)+=448.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09266892B2 |
|---|
| Source dataset | uspto-grants-2016_02 |
|---|
| ORD ID | ord-f4303696982f457c8b665477d819202e |
|---|
| Source note | uspto-grants-2016_02 |
|---|
