HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → tert-butyl 4-(4-(3-(1-(2,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | tert-butyl 4-(4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate | HCID 90030611 | — |
| Reactant | 1-[(2,5-Difluorophenyl)methyl]-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazole | HCID 90031187 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Ethanol toluene water | HCID 86587398 | — |
| Product | tert-butyl 4-(4-(3-(1-(2,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate | HCID 90033968 | 125.7% |
Reaction Steps
Using similar reaction conditions as described in step-ii of example-1, tert-butyl 4-(4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate (intermediate 41) (160 mg, 0.243 mmol) was coupled with 1-(2,5-difluorobenzyl)-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 25) (85 mg, 0.243 mmol) in sodium carbonate (77 mg, 0.729 mmol), Pd(PPh3)2Cl2 (17 mg, 0.0243 mmol), Toluene/ethanol/water (15/7.5/1 ml) to give 230 mg of titled compound. MS: m/z=753.1 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-5e44f0af532e467da6c6702d641c2c9a |
| Source note | uspto-grants-2016_05 |