Pyrrolidine → HCID 67155355, compound

HRID 389660Notes

Reaction equation

HRID 389660 reaction equation
[CH2:1]([S:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11](Br)[C:10]=1[Cl:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+]>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]>[CH2:1]([S:8][C:9]1[C:10]([Cl:17])=[C:11]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH:12]=[C:13]([F:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 67155224HCID 67155224, compound

Product 1

HCID 67155355HCID 67155355, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Intermediate 35 (1 g, 3.02 mmol), pyrrolidine (0,257 g, 3.62 mmol), Pd2dba3 (55 mg, 0.06 mmol, 2 mol-%), BINAP (75 mg, 0.12 mmol, 4 mol-%) and NaOtBu (376 mg, 3.92 mmol) were suspended in 25 ml of dry, degassed toluene and refluxed for 2 h under argon atmosphere. After full conversion the reaction mixture was chilled and purified by extraction with 30 ml H2O and ethyl acetate. The organic layer was dried with MgSO4 and evaporated to form an oil. The product was used without further purification in the next step.

Workup

  1. customof dry
  2. customdegassed toluene
  3. temperaturerefluxed for 2 h under argon atmosphere
  4. temperatureAfter full conversion the reaction mixture was chilled
  5. custompurified by extraction with 30 ml H2O and ethyl acetate
  6. dry with materialThe organic layer was dried with MgSO4
  7. customevaporated
  8. customto form an oil
  9. customThe product was used without further purification in the next step

Sources & evidence

ORD record
ord-aa519435dd8645caa814edd28cddd008
Source dataset
uspto-grants-2013_02
Patent number
US08378092B2

Reaction notes

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