Diethylamine → Methyl 3-amino-4-(2,6-dimethylphenylethynyl)-benzoate

HRID 1514929Notes

Reaction equation

HRID 1514929 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1I)[C:5]([O:7][CH3:8])=[O:6].[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=1[C:21]#[CH:22].C(NCC)C.C(OCC)(=O)C>CN(C=O)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I>[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:22]#[C:21][C:15]1[C:16]([CH3:20])=[CH:17][CH:18]=[CH:19][C:14]=1[CH3:13])[C:5]([O:7][CH3:8])=[O:6]

Participants

8

Reactant 4

HCID 8021DiethylamineHCID 8857Ethyl AcetateHCID 130076692-Ethynyl-1,3-dimethylbenzeneHCID 21628210Methyl 3-amino-4-iodobenzoate

Product 1

HCID 66965741Methyl 3-amino-4-(2,6-dimethylphenylethynyl)-benzoate

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 3-amino-4-iodobenzoate (920 mg, 3.32 mmol), 2,6-dimethylphenylacetylene (540 mg, 4.15 mmol),), bis-(triphenylphosphine) palladium (II) chloride (47 mg, 67 μmol), diethylamine (486 mg, 66 mmol), and copper (I) iodide (19 mg, 100 μmol) in DMF (10 mL) was heated at 120° C. in a microwave apparatus for 10 min. The mixture was poured into ethyl acetate and extracted six times with brine. The organic phase was dried, filtered, and the solvent was removed under reduced pressure to leave a residue that was chromatographed using a gradient of 0-30% heptane/ethyl acetate to afford methyl 3-amino-4-(2,6-dimethylphenylethynyl)-benzoate.

Workup

  1. extractionextracted six times with brine
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customto leave a residue that
  6. customwas chromatographed

Sources & evidence

ORD record
ord-1f95b15787b8488a885bd3de7e50aa83
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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