Sodium Carbonate → HCID 68805947, compound

HRID 2217563Notes

Reaction equation

HRID 2217563 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13](=[O:26])[NH:14][C:15]1[CH:20]=[CH:19][C:18](Br)=[CH:17][C:16]=1[C:22]([F:25])([F:24])[F:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27][S:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=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:26])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[S:28][CH3:27])=[CH:17][C:16]=1[C:22]([F:25])([F:24])[F:23])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27735432-(Methylthio)benzeneboronic acidHCID 68808135HCID 68808135, compound

Product 1

HCID 68805947HCID 68805947, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

2-(4-Bromo-2-trifluoromethyl-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.92 g, 4.4 mmol), 2-(methylthio)benzene boronic acid (0.88 g, 5.2 mmol), and tetrabutylammonium bromide (70 mg, 0.22 mmol) were combined in 40 mL toluene, added 4.4 mL of a 2M aqueous Na2CO3 solution followed by tetrakistriphenylphosphine palladium(0) (0.253 g, 0.22 mmol). Heated reaction at reflux 4 hours, 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% EtOAc in hexanes. Combined and concentrated pure fractions to yield title compound. (1.8 g, 85%) APCI (AP−): 479.1 (M−H)−.

Workup

  1. temperatureHeated
  2. customreaction
  3. temperatureat reflux 4 hours
  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% EtOAc in hexanes
  13. concentrationconcentrated pure fractions

Sources & evidence

ORD record
ord-57f4e1c49f93407a8c511801818abd48
Source dataset
uspto-grants-2008_08
Patent number
US07407974B2

Reaction notes

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