HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → N-(2-fluoro-5-(3-(1-(3-fluorobenzyl)-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 | N-(2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide | HCID 69206084 | — |
| Reactant | 5-bromo-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine | HCID 118200974 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Water 1,2-dimethoxyethane | HCID 18180031 | — |
| Product | N-(2-fluoro-5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide | HCID 90033300 | 94.6% |
Reaction Steps
Using similar reaction conditions as described in step-ii of example-1, 5-bromo-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (compound of Step-i of example 9) (166 mg, 0.317 mmol) was coupled with N-(2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide (Intermediate 65) (100 mg, 0.317 mmol) using sodium carbonate (101 mg, 0.952 mmol) and Pd(PPh3)2Cl2 (12 mg, 0.015 mmol) in DME/water (15/2 mL). This afforded 190 mg (94.5% yield) of the titled compound. MS: m/z=634.0 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-94182ce4534f4dc984e440e69c48ca8d |
| Source note | uspto-grants-2016_05 |