Benzocaine → HCID 22218329, compound

HRID 1795592Notes

Reaction equation

HRID 1795592 reaction equation
[CH3:1][C:2]1[C:3](OS(C(F)(F)F)(=O)=O)=[CH:4][C:5]2[C:6]([CH3:14])([CH3:13])[CH2:7][CH:8]=[C:9]([CH3:12])[C:10]=2[CH:11]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].[NH2:75][C:76]1[CH:86]=[CH:85][C:79]([C:80]([O:82][CH2:83][CH3:84])=[O:81])=[CH:78][CH:77]=1>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:3]([NH:75][C:76]2[CH:77]=[CH:78][C:79]([C:80]([O:82][CH2:83][CH3:84])=[O:81])=[CH:85][CH:86]=2)=[CH:4][C:5]2[C:6]([CH3:14])([CH3:13])[CH2:7][CH:8]=[C:9]([CH3:12])[C:10]=2[CH:11]=1

Participants

7

Reactant 4

HCID 2337BenzocaineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 59096158HCID 59096158, compound2×

Product 1

HCID 22218329HCID 22218329, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

General Procedure H A solution of trifluoromethanesulfonic acid 3,5,8,8-tetramethyl-7,8-dihydronaphthalen-2-yl ester (Compound 35, 0.41 g, 1.2 mmol), Pd(OAc)2 (0.027 g, 0.12 mmol), BINAP (0.11 g, 0.18 mmol), Cs2CO3 (0.56 g, 1.72 mmol), ethyl 4-aminobenzoate (0.25 g, 1.5 mmol) and 5 mL of toluene was flushed with argon for 10 min, then stirred at 100° C. in a sealed tube for 48 h. After the reaction mixture had been cooled to room temperature, the solvent was removed, and the residue was purified by flash column (hexane:ethyl acetate=4:1) to give 0.34 g (80%) of the title compound as a yellowish solid.

Workup

  1. temperatureAfter the reaction mixture had been cooled to room temperature
  2. customthe solvent was removed
  3. customthe residue was purified by flash column (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-49fe5bfe9da5431eb0fc684c84adf8b4
Source dataset
uspto-grants-2006_04
Patent number
US07026487B2

Reaction notes

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