Triethylamine → HCID 178432693, compound

HRID 2194385Notes

Reaction equation

HRID 2194385 reaction equation
I[C:2]1[NH:6][C:5]([CH3:7])=[N:4][CH:3]=1.C(N(CC)CC)C.[Cl:15][C:16]1[CH:17]=[C:18]([C:22]#[CH:23])[CH:19]=[CH:20][CH:21]=1>CN(C=O)C.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.[Cu]I>[Cl:15][C:16]1[CH:17]=[C:18]([C:22]#[C:23][C:2]2[N:6]=[C:5]([CH3:7])[NH:4][CH:3]=2)[CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 1230861-Chloro-3-ethynylbenzeneHCID 27946235-Iodo-2-methyl-1H-imidazole

Product 1

HCID 178432693HCID 178432693, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 500 mg (2.40 mmol) of 5-iodo-2-methyl-1H-imidazole (CAS: [73746-45-9]) in 7 ml of DMF were added under an argon atmosphere 118 mg (0.17 mmol) of Bis(triphenylphosphine)palladium dichloride and 0.67 ml (4.81 mmol) of triethylamine. The mixture was stirred for 10 min at room temperature. Then 0.52 ml (575 mg, 4.09 mmol) of 3-chloro-1-ethynyl-benzene and 13.7 mg (0.072 mmol) of copper(I) iodide were added and the mixture was stirred for 1.5 h at 60° C. The mixture was concentrated in vaccuo, dissolved in a minimal volume of methylene chloride and purified by chromatography on 20 g of silicagel (gradient Heptane/EtOAc 85:15->EtOAc) to yield 430 mg (83%) of the title compound as an orange crystalline solid, MS: m/e=217.2, 219.2 (M+H+).

Workup

  1. stirringthe mixture was stirred for 1.5 h at 60° C
  2. concentrationThe mixture was concentrated in vaccuo
  3. dissolutiondissolved in a minimal volume of methylene chloride
  4. custompurified by chromatography on 20 g of silicagel (gradient Heptane/EtOAc 85:15->EtOAc)

Sources & evidence

ORD record
ord-b395432deb6d4f14902a6f23b46c6184
Source dataset
uspto-grants-2012_12
Patent number
US08334287B2

Reaction notes

Loading…