Benzyl mercaptan → HCID 86687590, compound

HRID 1473533Notes

Reaction equation

HRID 1473533 reaction equation
Br[C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6]([Cl:13])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.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.[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[C:11]([CH3:12])=[C:10]2[C:5]([C:6]([Cl:13])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1)[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 455993807-Bromo-4-chloro-8-methylquinoline

Product 1

HCID 86687590HCID 86687590, compoundYield 99.2%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

To a vial charged with 7-bromo-4-chloro-8-methylquinoline (0.950 g, 3.70 mmol) was added Dioxane (14.81 ml), DIEA (1.294 ml, 7.41 mmol), xantphos (0.429 g, 0.741 mmol), Pd2(dba)3 (0.339 g, 0.370 mmol) and benzyl mercaptan (0.438 ml, 3.70 mmol). The vessel was sealed and heated to 110° C. for 3 hr 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 product as a yellow oil as a mixture of mono and bis substituted product according to MS as one LC peak, 7-(benzylthio)-4-chloro-8-methylquinoline (1.100 g, 3.67 mmol, 99% yield). m/z (ESI) 300.2 (M+H)+.

Workup

  1. customThe vessel was sealed
  2. customaffording complete conversion
  3. filtrationThe mixture was filtered through Celite
  4. customdried under reduced pressure
  5. custompurified with a 25 g Interchim column
  6. customaffording product as a yellow oil
  7. additionas a mixture of mono and bis

Sources & evidence

ORD record
ord-18c013936b0c44bd9d02c8ca8802f82f
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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