HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → (5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(4-pyridin-2-yl-[1,2,3]triazol-1-yl)-phenyl]amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | N-(4-Hydroxybenzyl)-4-[5-(1H-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-ylamino]benzamide | HCID 24857547 | — |
| Reactant | 5,8-Dibromoimidazo[1,2-a]pyrazine | HCID 53485949 | — |
| Reactant | 4-(4-Pyridin-2-yl-[1,2,3]triazol-1-yl)-phenylamine | HCID 59023133 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | (5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(4-pyridin-2-yl-[1,2,3]triazol-1-yl)-phenyl]amine | HCID 59023107 | — |
Reaction Steps
In the same way as described for Compound 90, step 1, using 5,8-dibromoimidazo[1,2-a]pyrazine (80.5 mg, 0.291 mmol), 4-(4-pyridin-2-yl-[1,2,3]triazol-1-yl)-phenylamine (68.3 g, 0.288 mmol), NaOtBu (38.2 mg, 0.403 mmol), Pd2(dba)3 (10.5 mg, 0.0115 mmol), Xantphos (13.3 mg, 0.023 mmol) and toluene (4 mL). The crude material is purified by silica gel column chromatography eluting with 98:2 DCM:MeOH followed by 97:3 DCM:MeOH affording the title compound (52.8 mg, 42%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08178530B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-f4321e980c8a488bb7089091b4379e76 |
| Source note | uspto-grants-2012_05 |