HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Bromoethanol → 2-(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl) ethanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Bromoethanol | HCID 10898 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine | HCID 90030300 | — |
| Reactant | 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine | HCID 90030931 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl) ethanol | HCID 118523979 | 52.7% |
Reaction Steps
Using similar reaction conditions as described in step-i of example-126, 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (step 1 compound of example 137) (150 mg, 0.297 mmol) was alkylated using 2-bromoethanol (62 mg, 0.494 mmol) and potassium carbonate (69 mg, 0.494 mmol) in DMF (1 ml) to afford 85 mg (52.7% yield) of the titled compound after purification by column (Silica gel 60/120) chromatography using 5% methanol in dichloromethane as eluent. MS: m/z=652.2 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353107B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-321f756ad07646f88211a750e2dfe435 |
| Source note | uspto-grants-2016_05 |