Triethylamine → 3-(5-Methylsulfanylpyridin-3-ylethynyl)-benzonitrile

HRID 606906Notes

Reaction equation

HRID 606906 reaction equation
C(N(CC)CC)C.Br[C:9]1[CH:10]=[N:11][CH:12]=[C:13]([S:15][CH3:16])[CH:14]=1.[C:17]([C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[C:22]#[N:23])#[CH:18]>C(OCC)(=O)C.[Cu]I.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:16][S:15][C:13]1[CH:14]=[C:9]([C:18]#[C:17][C:19]2[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=2)[C:22]#[N:23])[CH:10]=[N:11][CH:12]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 120889643-EthynylbenzonitrileHCID 223903593-Bromo-5-(methylthio)pyridine

Product 1

HCID 670477383-(5-Methylsulfanylpyridin-3-ylethynyl)-benzonitrileYield 41%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178419050HCID 178419050, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Add copper (I) iodide (20.0 mg, 0.18 mmol), bis(triphenylphosphine)palladium (II) dichloride (64.2 m g, 0.092 mmol) and triethylamine (1.03 mL, 7.32 mmol), to a solution of 3-bromo-5-methylsulfanylpyridine, (prepared as described in PREPARATION 29), (375 mg, 1.83 mmol) and 3-ethynylbenzonitrile, (prepared as described in PREPARATION 8), (465 mg, 3.66 mmol) in ethyl acetate (3 mL) and stir at 90° C. overnight. Cool to room temperature, concentrate and purify the residue by silica gel chromatography, eluting with hexanes/ethyl acetate, to give the title compound (187 mg, 41%).

Workup

  1. concentrationconcentrate
  2. custompurify the residue by silica gel chromatography
  3. washeluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-5375a83d112241129b1abe61742c4c3d
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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