Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Potassium vinyltrifluoroborate | HCID 23679353 | — |
| Reactant | HCID 67155879 | HCID 67155879 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Tetrahydrofuran 2-propanol | HCID 22597222 | — |
| Product | HCID 67155901 | HCID 67155901 | 57% |
Reaction Steps
2,6-Difluoro-N-(3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (0.050 g, 0.076 mmol), potassium vinyltrifluoroborate (0.012 g, 0.091 mmol), triethylamine (d. 0.726; 0.011 mL, 0.076 mmol) and PdCl2(dppf)*DCM (0.0031 g, 0.0038 mmol) were dissolved in 3:1 IPA/THF (1.0 mL), degassed with argon for 10 minutes and heated to 70° C. overnight. The solution was partitioned between water and EtOAc. The organic portion was washed with water (3×), brine, dried over Na2SO4 and concentrated. The resulting residue was purified by column chromatography (2:1 hexane/EtOAc) giving 2,6-difluoro-N-(1-(phenylsulfonyl)-3-vinyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide (57%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08338452B2 |
|---|
| Source dataset | uspto-grants-2012_12 |
|---|
| ORD ID | ord-ce70202b99da4304b67276d0b1d058bb |
|---|
| Source note | uspto-grants-2012_12 |
|---|
