Benzyl mercaptan → 7-(Benzylthio)-2-methoxy-4-(2-methoxy-4-(trifluoromethyl)phenyl)quinazoline

HRID 1473666Notes

Reaction equation

HRID 1473666 reaction equation
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.Br[C:44]1[CH:53]=[C:52]2[C:47]([C:48]([C:56]3[CH:61]=[CH:60][C:59]([C:62]([F:65])([F:64])[F:63])=[CH:58][C:57]=3[O:66][CH3:67])=[N:49][C:50]([O:54][CH3:55])=[N:51]2)=[CH:46][CH:45]=1.CCN(C(C)C)C(C)C.[CH2:77]([SH:84])[C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1>O1CCOCC1.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]>[CH2:77]([S:84][C:44]1[CH:53]=[C:52]2[C:47]([C:48]([C:56]3[CH:61]=[CH:60][C:59]([C:62]([F:65])([F:64])[F:63])=[CH:58][C:57]=3[O:66][CH3:67])=[N:49][C:50]([O:54][CH3:55])=[N:51]2)=[CH:46][CH:45]=1)[C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1

Participants

7

Reactant 4

HCID 7509Benzyl mercaptanHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 866877417-Bromo-2-methoxy-4-(2-methoxy-4-(trifluoromethyl)phenyl)quinazoline

Product 1

HCID 866877427-(Benzylthio)-2-methoxy-4-(2-methoxy-4-(trifluoromethyl)phenyl)quinazoline

Reagents, catalysts & solvents 2

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

Procedure

A solution of Pd2(dba)3 (9.20 mg, 10.04 μmol), Xantphos (0.012 g, 0.020 mmol), 7-bromo-2-methoxy-4-(2-methoxy-4-(trifluoromethyl)phenyl)quinazoline (0.166 g, 0.402 mmol), and n,n-diisopropylethylamine (0.211 ml, 1.205 mmol) in 2 mL dioxane was heated to 60° C. and was treated with benzyl mercaptan (0.048 ml, 0.402 mmol). After stirring for one hour, LC/MS showed mostly product, so the reaction mixture was concentrated. This material was carried on to step 5 without purification. (M+H)+=457.2.

Workup

  1. concentrationso the reaction mixture was concentrated
  2. customThis material was carried on to step 5 without purification

Sources & evidence

ORD record
ord-19d408f3a8624849aba5853bb2b54a71
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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