Hydrochloric Acid → HCID 21856040, compound

HRID 2229522Notes

Reaction equation

HRID 2229522 reaction equation
C(N([CH2:6][CH3:7])CC)C.[CH2:8]([O:10][C:11](=[O:19])[C:12]1[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=1)[CH3:9].Cl>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:8]([O:10][C:11](=[O:19])[C:12]1[CH:17]=[CH:16][C:15]([C:11]2[O:10][C:7]3[CH:6]=[CH:16][CH:15]=[CH:14][C:13]=3[CH:12]=2)=[CH:14][CH:13]=1)[CH3:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 142891Ethyl 4-iodobenzoate

Product 1

HCID 21856040HCID 21856040, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

The compound prepared in Reference Example 1 (2.64 g), dichlorobis(triphenylphosphine)palladium (II) [PdCl2(PPh3)2] (0.635 g) and triethylamine (10 ml) were added to a solution of 4-iodobenzoic acid ethyl ester (5 g) in dimethylformamide (10 ml). The mixture was stirred at 80° C. for 6 hours. To the reaction mixture, 1N hydrochloric acid was added. The mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated. The precipitated crystals was washed with hexane/diethyl ether and dried to give the title compound (3.6 g) having the following physical data.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. washThe precipitated crystals was washed with hexane/diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-27b29679871d44d3b7ceab125271285f
Source dataset
uspto-grants-2002_07
Patent number
US06420427B1

Reaction notes

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