3-Iodotoluene → HCID 86616591, compound

HRID 2100474Notes

Reaction equation

HRID 2100474 reaction equation
I[C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.[C:9]([C:11]1[C:12]([NH:17][C:18](=[O:23])[CH2:19][CH2:20][C:21]#[CH:22])=[N:13][CH:14]=[CH:15][CH:16]=1)#[N:10]>C(NCC)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>[C:9]([C:11]1[C:12]([NH:17][C:18](=[O:23])[CH2:19][CH2:20][C:21]#[C:22][C:2]2[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=2)=[N:13][CH:14]=[CH:15][CH:16]=1)#[N:10]

Participants

6

Reactant 2

HCID 122683-IodotolueneHCID 86616592HCID 86616592, compound

Product 1

HCID 86616591HCID 86616591, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Procedure

Under an atmosphere of argon, bis(triphenylphosphine)palladium(II) chloride ([13965-03-2], 326 mg) and copper(I) iodide (44 mg) were added to a solution of 3-iodotoluene ([625-95-6], 506 mg, 2 mmol) and pent-4-ynoic acid (3-cyano-pyridin-2-yl)-amide (508 mg, 3 mmol) in diethylamine (15 ml). The mixture was kept at r.t. (3d). The volatiles were evaporated, and the residue was taken up in ethyl acetate. After washing (H2O) and drying (Na2SO4), the solvent was evaporated and 5-m-tolyl-pent-4-ynoic acid (3-cyano-pyridin-2-yl)-amide was isolated from the reaction mixture by column chromatography (silica gel, ethyl acetate/heptane). MS: m/e=290.1 [M+H+].

Workup

  1. customwas kept at r.t.
  2. customThe volatiles were evaporated
  3. washAfter washing (H2O)
  4. dry with materialdrying (Na2SO4)
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-da63100db0f84adcb3eb65b1c3637967
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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