Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzyl mercaptan | HCID 7509 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | HCID 86687527 | HCID 86687527 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Product | HCID 86687529 | HCID 86687529 | 78.5% |
Reaction Steps
To a 2-5 ml microwave vial charged with 7-chloro-4-(2-methoxy-4-(trifluoromethyl)phenyl)cinnoline (0.140 g, 0.413 mmol) was added Xantphos (0.048 g, 0.083 mmol), Pd2(dba)3 (0.038 g, 0.041 mmol), dioxane (1.653 ml) DIEA (0.144 ml, 0.827 mmol) and benzyl mercaptan (0.051 ml, 0.434 mmol). The mixture was purged with argon and microwave irradiated at 140° C. for 10 hrs. The mixture was filtered through diatomaceous earth, dried under reduced pressure and the crude residue purified with a 40 g HP silicycle column (SiliCycle, Inc. Quebec City, Canada) ramping EtOAc in heptane (0 to 50%, 5% DCM throughout) providing 7-(benzylthio)-4-(2-methoxy-4-(trifluoromethyl)phenyl)cinnoline (0.138 g, 0.324 mmol, 78% yield) as an off-white solid. m/z (ESI) 427.3 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09012443B2 |
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| Source dataset | uspto-grants-2015_04 |
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| ORD ID | ord-6bcfe55e837e4883b3f9c87d93bf47c4 |
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| Source note | uspto-grants-2015_04 |
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