HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → N-(2-methoxy-5-(3-(1-phenethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1-(2-phenylethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 70929327 | — |
| Reactant | N-(5-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methanesulfonamide | HCID 90030027 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Ethanol toluene water | HCID 86587398 | — |
| Product | N-(2-methoxy-5-(3-(1-phenethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide | HCID 118523955 | 103.5% |
Reaction Steps
Using similar reaction conditions as described in step-ii of example-1, N-(5-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-methoxyphenyl)methanesulfonamide (Intermediate 23) (90 mg, 0.1506 mmol) was coupled with 1-phenethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 59) (67 mg, 0.225 mmol) using Pd(PPh3)2Cl2 (6 mg, 0.05 mmol) and sodium carbonate (40 mg, 0.376 mmol) in toluene/ethanol/water (3/2/1 ml) to afford 100 mg of the crude compound. MS: m/z=642.7 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-a93dd3244f304386aac145025585cdcf |
| Source note | uspto-grants-2016_05 |