2-Iodotoluene → 2,3-Dimethoxy-5-[(2-methylphenyl)ethynyl]pyridine

HRID 709048Notes

Reaction equation

HRID 709048 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([O:11][CH3:12])[C:6]([O:9][CH3:10])=[N:7][CH:8]=1)#[CH:2].ClCCl.I[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23]>C(N(CC)CC)C.C(OCC)(=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>[CH3:10][O:9][C:6]1[C:5]([O:11][CH3:12])=[CH:4][C:3]([C:1]#[C:2][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])=[CH:8][N:7]=1

Participants

8

Reactant 3

HCID 51282-IodotolueneHCID 6344DichloromethaneHCID 582133895-Ethynyl-2,3-dimethoxypyridine2×

Product 1

HCID 711862092,3-Dimethoxy-5-[(2-methylphenyl)ethynyl]pyridineYield 56%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Bis(triphenylphosphine)palladium(II) dichloride (50 mg, 0.07 mmol), copper (I) iodide (25 mg, 0.13 mmol) and 5-ethynyl-2,3-dimethoxypyridine (Intermediate 32) (500 mg, 3.1 mmol) were suspended in degassed triethylamine (5 ml) and dichloromethane (5 ml) to give a brown suspension. To this was added 1-iodo-2-methylbenzene (670 mg, 3.1 mmol) by syringe and the reaction was allowed to stir for 16 hours before being diluted with ethyl acetate and washed with brine. The crude material was purified by column chromatography (SiO2; 0-10% ethyl acetate in petrol) to afford 2,3-dimethoxy-5-[(2-methylphenyl)ethynyl]pyridine (437 mg, 56% yield).

Workup

  1. washwashed with brine
  2. customThe crude material was purified by column chromatography (SiO2; 0-10% ethyl acetate in petrol)

Sources & evidence

ORD record
ord-a8ad6790e9884a6594565c890f2fe48a
Source dataset
uspto-grants-2015_11
Patent number
US09180122B2

Reaction notes

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