Triethylamine → HCID 19363124, compound

HRID 850318Notes

Reaction equation

HRID 850318 reaction equation
[CH3:1][N:2]([CH3:26])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:9]=[C:10]([CH:15]=[C:16](OS(C(F)(F)F)(=O)=O)[CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])=[O:7].[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=1B(O)O.C(N(CC)CC)C>CN(C)C=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>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=1[C:16]1[CH:17]=[C:8]([C:6](=[O:7])[NH:5][CH2:4][CH2:3][N:2]([CH3:26])[CH3:1])[CH:9]=[C:10]([CH:15]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27733712,5-Dichlorobenzeneboronic acidHCID 19363121HCID 19363121, compound

Product 1

HCID 19363124HCID 19363124, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 3-((2-dimethylaminoethyl)carbamoyl]-5-(trifluoromethylsulfonyloxy)benzoate (2 g), 2,5-dichlorophenyl-dihydroxyborane 1.25 g), tetrakis(triphenylphosphine)palladium(0) (0.17 g) and triethylamine (1.52 g) in N,N-dimethylformamide (40 ml) was heated at 100° C. for 3 hours under nitrogen atmosphere. After evaporating the solvent, the residue was dissolved in a mixture of ethyl acetate (100 ml) and water (100 ml). The organic layer was successively washed with 10% potassium carbonate aqueous solution, brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel (100 ml) eluting with a mixture of chloroform and methanol (20:1). The fractions containing the desired products were collected and evaporated in vacuo. The residue was crystallized from diisopropyl ether to afford methyl 5-(2,5-dichlorophenyl)-3-[(2-dimethylaminoethyl)carbamoyl]benzoate.

Workup

  1. customAfter evaporating the solvent
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate (100 ml) and water (100 ml)
  3. washThe organic layer was successively washed with 10% potassium carbonate aqueous solution, brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by column chromatography on silica gel (100 ml)
  7. washeluting with a mixture of chloroform and methanol (20:1)
  8. additionThe fractions containing the desired products
  9. customwere collected
  10. customevaporated in vacuo
  11. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-7af2bdc0e5194893898d61f1897dd8da
Source dataset
uspto-grants-2000_01
Patent number
US06017917

Reaction notes

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