Benzyl mercaptan → 7-(Benzylthio)-4-(2-methoxy-4-(trifluoromethyl)phenyl)-2-methylquinazoline
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:55]3[CH:60]=[CH:59][C:58]([C:61]([F:64])([F:63])[F:62])=[CH:57][C:56]=3[O:65][CH3:66])=[N:49][C:50]([CH3:54])=[N:51]2)=[CH:46][CH:45]=1.CCN(C(C)C)C(C)C.[CH2:76]([SH:83])[C:77]1[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=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]>[CH2:76]([S:83][C:44]1[CH:53]=[C:52]2[C:47]([C:48]([C:55]3[CH:60]=[CH:59][C:58]([C:61]([F:64])([F:63])[F:62])=[CH:57][C:56]=3[O:65][CH3:66])=[N:49][C:50]([CH3:54])=[N:51]2)=[CH:46][CH:45]=1)[C:77]1[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of Pd2(dba)3 (0.046 g, 0.050 mmol), Xantphos (0.058 g, 0.100 mmol), 7-bromo-4-(2-methoxy-4-(trifluoromethyl)phenyl)-2-methylquinazoline (0.797 g, 2.007 mmol), and n,n-diisopropylethylamine (1.051 ml, 6.02 mmol) in 10 mL dioxane was heated to 60° C. and was treated with benzyl mercaptan (0.237 ml, 2.007 mmol). After stirring for one hour, LC/MS showed mostly product, so the reaction mixture was concentrated. This material was carried on to step 3 without purification. (M+H)+=441.0.
Workup
- concentrationso the reaction mixture was concentrated
- customThis material was carried on to step 3 without purification
Sources & evidence
- ORD record
- ord-481b9e8366194ac5b2076a7280687da2
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012443B2
Reaction notes
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