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Ethanethiol → 5-Ethylsulfanyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

HRID 1930814
Notes
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Reaction equation

HRID 1930814 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 6343EthanethiolHCID 16102683N-Boc-5-bromoisoindolineHCID 23676156Sodium t-butoxide

Product 1

HCID 577536005-Ethylsulfanyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalyst
HCID 15420033
Bis(cyclopenta-2,4-dien-1-yl-di(propan-2-yl)phosphane);iron(2+)
Catalyst
HCID 312751,4-DioxaneSolvent
HCID 21939870Tetrahydrofuran ethyl acetateSolvent

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

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. washwashed with brine
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ce8b68a559d4ea68f089b0496c5fbda
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08188139B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes