Diisopropylethylamine → HCID 87279450, compound
Reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]([NH:6][CH2:7][CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[C:4]([S:16]([F:21])([F:20])([F:19])([F:18])[F:17])[CH:3]=1.[C:22](=[S:25])([O-:24])[CH3:23].[K+].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(N(CC)C(C)C)(C)C>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]>[C:22]([O:24][C:2]1[CH:15]=[CH:14][C:5]([NH:6][CH2:7][CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[C:4]([S:16]([F:21])([F:20])([F:19])([F:18])[F:17])[CH:3]=1)(=[S:25])[CH3:23]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
To a solution of EXAMPLE 233C (456 mg) and potassium ethanethioate (197 mg) in dioxane (4 mL) was added tris(dibenzylideneacetone)dipalladium(0) (27 mg) and xantphos (33 mg) followed by N,N-diisopropylethylamine (0.5 mL). The mixture was purged with argon, sealed and stirred under microwave irradiation for 60 minutes at 120° C. The mixture was dissolved in ethyl acetate (300 mL) and water (100 mL). The organic phase was washed with brine and dried over Na2SO4. Filtration and evaporation of the solvent followed by flash chromatography (20% ethyl acetate in hexane) provided the title compound.
Workup
- customThe mixture was purged with argon
- customsealed
- dissolutionThe mixture was dissolved in ethyl acetate (300 mL)
- washThe organic phase was washed with brine
- dry with materialdried over Na2SO4
- filtrationFiltration and evaporation of the solvent
Sources & evidence
- ORD record
- ord-717685f822064442806d523eb1c616b9
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546399B2
Reaction notes
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