Sodium Carbonate → HCID 58695797, compound

HRID 1178888Notes

Reaction equation

HRID 1178888 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[C:14](=[O:17])[CH2:15][CH3:16])(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].CC1(C)C(C)(C)OB([C:34]2[CH2:40][CH:39]3[N:41]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH:36]([CH2:37][CH2:38]3)[CH:35]=2)O1.FC(F)(F)S([O-])(=O)=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C1(C)C=CC=CC=1.C(O)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:34]2[CH2:35][CH:36]3[N:41]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH:39]([CH2:38][CH2:37]3)[CH:40]=2)=[C:8]([C:14](=[O:17])[CH2:15][CH3:16])[CH:9]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 2758875TrifluoromethanesulfonateHCID 58695789HCID 58695789, compoundHCID 58695820HCID 58695820, compound

Product 1

HCID 58695797HCID 58695797, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of 4-chloro-2-propionylphenyl trifluoromethanesulfonate (2-5) (21.0 g, 66.3 mmol), absolute ethanol (120 mL), toluene (120 mL), and 2M aqueous solution of sodium carbonate (100 mL) was added ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate (2-3) (20.3 g, 66.3 mmol). The mixture was evacuated and flushed with nitrogen three times. After addition of tetrakis(triphenylphosphine)palladium(0) (7.69 g, 6.63 mmol), the mixture was heated at 75° C. for 1 h and TLC showed no remaining trifluoromethanesulfonate. After cooling to room temperature, the mixture was poured into water and extracted with EtOAc (3×250 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated. Purification of the crude residue by flash chromatography over silica gel (10% ethyl acetate/hexanes as eluent) afforded (2-6) as a colorless oil.

Workup

  1. customThe mixture was evacuated
  2. customflushed with nitrogen three times
  3. temperatureAfter cooling to room temperature
  4. extractionextracted with EtOAc (3×250 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification of the crude residue by flash chromatography over silica gel (10% ethyl acetate/hexanes as eluent)

Sources & evidence

ORD record
ord-325349f7502b4963a08083ec47b6dbcd
Source dataset
uspto-grants-2007_10
Patent number
US07276520B2

Reaction notes

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