Ethanethiol → 5-Ethylsulfanyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[Na+].[CH2:24]([SH:26])[CH3:25]>O1CCOCC1.C(OCC)(=O)C.O1CCCC1.C(P(C(C)C)[C-]1C=CC=C1)(C)C.[C-]1(P(C(C)C)C(C)C)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([S:26][CH2:24][CH3:25])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
8
Reactant 3
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 100 °C
Procedure
Lit. Tetrahedron 2004, 60, 7397-7403. To a stirred suspension of 1.34 mmol 5-bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (CAS: 201940-08-1) in 2 ml dioxane were added 0.03 mmol 1,1′-bis(diisopropylphosphino)ferrocene, 0.03 mmol palladium acetate, 1.61 mmol sodium tert-butoxide and 2.68 mmol ethanethiol and the mixture was stirred at 100° C. for 16 h. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate/tetrahydrofuran and washed with brine. The organic phase was dried over sodium sulfate and concentrated in vacuo to yield the title compound as a brown oil which was used in the next step without further purification.
Workup
- temperatureThe reaction mixture was then cooled to room temperature
- washwashed with brine
- dry with materialThe organic phase was dried over sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-8ce8b68a559d4ea68f089b0496c5fbda
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188139B2
Reaction notes
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