Benzyl mercaptan → HCID 86687529, compound

HRID 1473479Notes

Reaction equation

HRID 1473479 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=3[O:22][CH3:23])=[CH:7][N:8]=[N:9]2)=[CH:4][CH:3]=1.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.O1CCOCC1.[CH2:72]([SH:79])[C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=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]>[CH2:72]([S:79][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=3[O:22][CH3:23])=[CH:7][N:8]=[N:9]2)=[CH:4][CH:3]=1)[C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1

Participants

6

Reactant 4

HCID 7509Benzyl mercaptanHCID 312751,4-DioxaneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86687527HCID 86687527, compound

Product 1

HCID 86687529HCID 86687529, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

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)+.

Workup

  1. customThe mixture was purged with argon and microwave
  2. customirradiated at 140° C. for 10 hrs
  3. filtrationThe mixture was filtered through diatomaceous earth
  4. customdried under reduced pressure
  5. customthe crude residue purified with a 40 g HP silicycle column (SiliCycle, Inc. Quebec City, Canada)

Sources & evidence

ORD record
ord-6bcfe55e837e4883b3f9c87d93bf47c4
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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