Benzyl mercaptan → HCID 86687580, compound

HRID 1473524Notes

Reaction equation

HRID 1473524 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Cl:12])=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH3:13].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CCN(C(C)C)C(C)C.[CH2:65]([SH:72])[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH2:65]([S:72][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Cl:12])=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH3:13])[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1

Participants

7

Reactant 4

HCID 7509Benzyl mercaptanHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 455993917-Bromo-4-chloro-6-methylquinoline

Product 1

HCID 86687580HCID 86687580, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a flask charged with 7-bromo-4-chloro-6-methylquinoline (0.240 g, 0.936 mmol) was added Xantphos (0.108 g, 0.187 mmol), Pd2(dba)3 (0.086 g, 0.094 mmol), dioxane (3.74 ml), DIEA (0.327 ml, 1.871 mmol) and benzyl mercaptan (0.111 ml, 0.936 mmol). The vessel was heated at 110° C. for 2 hr affording conversion to desired product. The mixture was cooled to room temperature, 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 product as a yellow solid with minor impurities, 7-(benzylthio)-4-chloro-6-methylquinoline (0.287 g, 0.957 mmol, 102% yield). m/z (ESI) 300.0 (M+H)+.

Sources & evidence

ORD record
ord-edb8600bd9774659b11292830cc3c41c
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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