Benzyl mercaptan → HCID 86687585, compound

HRID 1473528Notes

Reaction equation

HRID 1473528 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[O:13][CH3:14].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.[CH2:66]([SH:73])[C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=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>[CH2:66]([S:73][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[O:13][CH3:14])[C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1

Participants

7

Reactant 4

HCID 7509Benzyl mercaptanHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 866875847-bromo-4-chloro-6-methoxyquinoline

Product 1

HCID 86687585HCID 86687585, compoundYield 115.8%

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-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)+.

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

Sources & evidence

ORD record
ord-c744426b3b484742804a78f5e6159aea
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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