HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → HCID 90030381, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | HCID 90022686 | HCID 90022686 | — |
| Reactant | 5-bromo-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine | HCID 118200974 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethanol toluene water | HCID 86587398 | — |
| Product | HCID 90030381 | HCID 90030381 | 56.9% |
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) (100 mg, 0.190 mmol) was coupled with 2-(4-(2-(methylsulfonamido)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazin-1-yl)acetamide (Intermediate 65A) 125 mg, 0.285 mmol) using sodium carbonate (60 mg, 0.567 mmol) and Pd(PPh3)4 (11 mg, 0.0095 mmol) in toluene/ethanol/water (2/2/1 mL). This afforded 82 mg (56.9% yield) after preparative TLC (Silicagel-1000 micron) using 5% ammoniated methanol in DCM as eluent. MS: m/z=757.2 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-600708e16f694618a63702811c5721ce |
| Source note | uspto-grants-2016_05 |