Benzyl mercaptan → 3-[2-Methyl-3-[(phenylmethyl)thio]phenyl]pyridine
Reaction equation
Br[C:2]1[C:3]([CH3:14])=[C:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[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]([CH3:14])=[C:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[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 73 (3 g, 12.09 mmol) in dioxane (50 ml) was stirred under argon, then DIPEA (3.82 ml, 24.18 mmol), xantphos (0.42 g, 0.73 mmol) and Pd2(dba)3 (0.33 g, 0.36 mmol) were added and the reaction was heated to 100° C. Phenyl-methanethiol (1.56 ml, 13.3 mmol) was slowly added and the reaction stirred for 16 h. The reaction was quenched by addition of 150 ml of H2O. After extraction (three times) with ethyl acetate the combined organic layers were washed with water, dried with Na2SO4, evaporated to dryness and the compound was obtained and used without further purification in step 22.3.
Workup
- customThe reaction was quenched by addition of 150 ml of H2O
- extractionAfter extraction (three times) with ethyl acetate the combined organic layers
- washwere washed with water
- dry with materialdried with Na2SO4
- customevaporated to dryness
- customthe compound was obtained
- customused without further purification in step 22.3
Sources & evidence
- ORD record
- ord-c20ad7ace3154239a4508337e017510f
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08378092B2
Reaction notes
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