Sodium Sulfate → HCID 68949069, compound

HRID 238984Notes

Reaction equation

HRID 238984 reaction equation
Br[C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C@@H:18]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH3:25])[CH2:19]3)=[CH:14][CH:13]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1.C([O-])(C)(C)C.[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH2:23]([N:20]1[CH2:21][CH2:22][C@@H:18]([C:15]2[CH:16]=[CH:17][C:12]([NH:11][S:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)[CH:3]=3)(=[O:10])=[O:9])=[CH:13][CH:14]=2)[CH2:19]1)[CH2:24][CH3:25]

Participants

7

Reactant 5

HCID 24436Sodium SulfateHCID 31268PyrrolidineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 68952143HCID 68952143, compound

Product 1

HCID 68949069HCID 68949069, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

0.4 g of 3-Bromo-N-[4-((S)-1-propyl-pyrrolidin-3-yl)-phenyl]-benzenesulfonamide (0.94 mmol), 0.156 ml pyrrolidin (1.89 mmol), 160 mg sodium tert-butanolate ((1.66 mmol) and 540 mg sodium sulfate were dissolved in 15 ml of tetrahydrofuran and heated to 50° C. 120 mg of 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (0.19 mmol) and 85 mg tri(dibenzylidenacetone)dipalladium(0) (0.09 mmol) were added and the reaction stirred for 4 h under reflux. After workup, the partially converted starting material was reacted again under the same reaction conditions until completion. The solvents were evaporated under reduced pressure, the residue was treated with dichloromethane and water, the organic layer was dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The crude product was purified with silica gel chromatography with dichloromethane/methanol (0-20%) as eluent using a semi-automated ISCO companion instrument, yielding 0.309 g of the purified product.

Workup

  1. temperatureunder reflux
  2. customwas reacted again under the same reaction conditions until completion
  3. customThe solvents were evaporated under reduced pressure
  4. additionthe residue was treated with dichloromethane and water
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customThe crude product was purified with silica gel chromatography with dichloromethane/methanol (0-20%) as eluent

Sources & evidence

ORD record
ord-5ddddfc9f7ba4559995897ccf2bfb283
Source dataset
uspto-grants-2014_02
Patent number
US08642642B2

Reaction notes

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