Sodium Carbonate → HCID 68805998, compound

HRID 2217424Notes

Reaction equation

HRID 2217424 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13](=[O:23])[NH:14][C:15]1[CH:20]=[CH:19][C:18](Br)=[CH:17][C:16]=1[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][S:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=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:23])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[S:25][CH3:24])=[CH:17][C:16]=1[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27735432-(Methylthio)benzeneboronic acidHCID 68808253HCID 68808253, compound

Product 1

HCID 68805998HCID 68805998, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

2-(4-Bromo-2-methyl-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.07 g, 2.7 mmol), 2-(methylthio)benzene boronic acid (0.56 g, 3.3 mmol), and tetrabutylammonium bromide (322 mg, 0.13 mmol) were combined in 20 mL toluene, added 2.8 mL of a 2M aqueous Na2CO3 solution followed by tetrakistriphenylphosphine palladium(0) (0.161 g, 0.13 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. (0.59 g, 50%) APCI (AP−): 425.1 (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-ab6b3f8ddcbf43349ced2aae544bf800
Source dataset
uspto-grants-2008_08
Patent number
US07407972B2

Reaction notes

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