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

HRID 1514934Notes

Reaction equation

HRID 1514934 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].[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=1[C:21]#[CH:22].C(NCC)C>C(#N)C.C(#N)C.C(#N)C.[Pd](Cl)Cl.[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:14]([Cl:13])=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:20])[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 3

HCID 8021DiethylamineHCID 21628210Methyl 3-amino-4-iodobenzoateHCID 22271730Benzene, 1,3-dichloro-2-ethynyl-

Product 1

HCID 66966063Methyl 3-amino-4-(2,6-dichlorophenylethynyl)-benzoate

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6093782Bis(acetonitrile)dichloropalladiumCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of methyl 3-amino-4-iodobenzoate (604 mg, 2.18 mmol) (from Example 3-4), 2,6-dichlorophenylacetylene (447 mg, 2.61 mmol), palladium (II) chloride bis(acetonitrile) (23 mg, 89 μmol), diethylamine (449 μL, 318 mg, 4.35 mmol), and copper (I) iodide (21 mg, 110 μmol) in acetonitrile (10 mL) was heated for 35 min at 120° C. in a microwave apparatus. The mixture was filtered, and the filtrate concentrated, then chromatographed using a gradient of 0-30% heptane/ethyl acetate to give methyl 3-amino-4-(2,6-dichlorophenylethynyl)-benzoate.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated
  3. customchromatographed

Sources & evidence

ORD record
ord-ccc0e3edc632437db918d2fabb7704a6
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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