Sodium Carbonate → HCID 68808158, compound

HRID 1796250Notes

Reaction equation

HRID 1796250 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13](=[O:22])[NH:14][C:15]1[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:23][S:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13](=[O:22])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[S:24][CH3:23])=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 551020HCID 551020, compoundHCID 27735432-(Methylthio)benzeneboronic acid

Product 1

HCID 68808158HCID 68808158, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

2-(4-Bromo-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (2.57 g, 6.9 mmol), 2-(methylthio)benzene boronic acid (1.4 g, 8.3 mmol), and tetrabutylammonium bromide (110 mg, 0.33 mmol) were combined in 30 mL toluene, added 6.9 mL of a 2M aqueous Na2CO3 solution followed by tetrakistriphenylphosphine palladium(0) (0.40 g, 0.34 mmol). Heated reaction at reflux overnight, cooled, concentrated, redissolved in EtOAc (250 mL), washed with water (3×200 mL), brine (200 mL), dried with MgSO4, filtered, and concentrated. Purified on a silica gel column eluted with 20% moving to 40% EtOAc in hexanes. Combined and concentrated pure fractions to yield title compound. (1.75 g, 60%) APCI (AP−): 411.1 (M−H)−.

Workup

  1. temperatureHeated
  2. customreaction
  3. temperatureat reflux overnight
  4. temperaturecooled
  5. concentrationconcentrated
  6. dissolutionredissolved in EtOAc (250 mL)
  7. washwashed with water (3×200 mL), brine (200 mL)
  8. dry with materialdried with MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurified on a silica gel column
  12. washeluted with 20%
  13. concentrationconcentrated pure fractions

Sources & evidence

ORD record
ord-abe2aa28442f4aa2a1d7c654798fd049
Source dataset
uspto-grants-2006_04
Patent number
US07030141B2

Reaction notes

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