Benzyl mercaptan → 1-(3-Benzylsulfanyl-2-fluoro-phenyl)-pyrrolidin-2-one
Reaction equation
Br[C:2]1[C:3]([F:14])=[C:4]([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])[CH:5]=[CH:6][CH:7]=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.[C:66]1([CH2:72][SH:73])[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=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]>[CH2:72]([S:73][C:2]1[C:3]([F:14])=[C:4]([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])[CH:5]=[CH:6][CH:7]=1)[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
Intermediate 98 (1.48 g, 5.73 mmol) in dioxane (50 ml) was stirred under argon. DIPEA (2 ml, 11.47 mmol), xantphos (0.2 g, 0.34 mmol) and Pd2(dba)3 (0.157 g, 0.17 mmol) were added and the reaction was heated to 100° C. Phenyl-methanethiol (0.64 ml, 5.45 mmol) was slowly added and the reaction stirred for 1 h. The reaction was quenched by the addition of 50 ml of H2O. After extraction with ethyl acetate (three times) the combined organic layers were washed with water, dried with Na2SO4, evaporated to dryness and the product was purified by silica gel chromatography.
Workup
- customThe reaction was quenched by the addition of 50 ml of H2O
- extractionAfter extraction with ethyl acetate (three times) the combined organic layers
- washwere washed with water
- dry with materialdried with Na2SO4
- customevaporated to dryness
- customthe product was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-c2860cbdf4814a9ab7a1f5d279200616
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08378092B2
Reaction notes
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