Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzyl mercaptan | HCID 7509 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 7-bromo-4-chloro-6-methoxyquinoline | HCID 86687584 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86687585 | HCID 86687585 | 115.8% |
Reaction Steps
To a vial charged with 7-bromo-4-chloro-6-methoxyquinoline (0.240 g, 0.881 mmol) was added Dioxane (3.52 ml), DIEA (0.308 ml, 1.761 mmol), Xantphos (0.102 g, 0.176 mmol), Pd2(dba)3 (0.081 g, 0.088 mmol) and benzyl mercaptan (0.104 ml, 0.881 mmol). The vessel was sealed and heated to 110° C. for 90 mins affording complete conversion according to LC-MS. The mixture was filtered through Celite and dried under reduced pressure and purified with a 25 g Interchim column ramping EtOAc in heptane (0-50%, 10% DCM throughout) affording 7-(benzylthio)-4-chloro-6-methoxyquinoline (322 mg, 1.020 mmol, quant. yield) as a yellow solid with minor impurity. m/z (ESI) 316.3 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09012443B2 |
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| Source dataset | uspto-grants-2015_04 |
|---|
| ORD ID | ord-c744426b3b484742804a78f5e6159aea |
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| Source note | uspto-grants-2015_04 |
|---|
