Acetonitrile → 4-(2,4-Dimethoxy-3-fluoro-phenylethynyl)-1-methyl-1H-pyrazole

HRID 1042579Notes

Reaction equation

HRID 1042579 reaction equation
[CH3:1][O:2][C:3]1[C:8]([F:9])=[C:7]([O:10][CH3:11])[CH:6]=[CH:5][C:4]=1I.[C:13]([C:15]1[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=1)#[CH:14].C(#N)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(N(CC)CC)C>[CH3:1][O:2][C:3]1[C:8]([F:9])=[C:7]([O:10][CH3:11])[CH:6]=[CH:5][C:4]=1[C:14]#[C:13][C:15]1[CH:16]=[N:17][N:18]([CH3:20])[CH:19]=1

Participants

7

Reactant 3

HCID 6342AcetonitrileHCID 509982281,3-Dimethoxy-2-fluoro-4-iodobenzeneHCID 511383214-Ethynyl-1-methyl-1H-pyrazole

Product 1

HCID 687686434-(2,4-Dimethoxy-3-fluoro-phenylethynyl)-1-methyl-1H-pyrazoleYield 86%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

To a mixture of (0.95 mmol) of 2,4-dimethoxy-3-fluoro-iodo benzene, 0.122 g (1.15 mmol) of 4-ethynyl-1-methyl-1H-pyrazole, 0.028 g (0.04 mmol) of dichlorobis(triphenylphosphine)palladium (II) and 8 mg (0.042 mmol) of copper (I) iodide 4 mL of anhydrous acetonitrile and 2 mL of triethylamine were added under nitrogen atmosphere at room temperature. The resulting mixture was stirred for 1 hour, when TLC indicated a consumption of the iodobenzene. The solvent was evaporated under reduced pressure and the residue purified by flash column chromatography (silica gel; dichloromethane:ethyl acetate 9:1) to give the title compound in an 86% yield as creamy crystals. H1 NMR (CDCl3) 3.88 (s, 3H, Me); 3.89 (s, 3H, MeO); 4.05 (d, 3H, MeO, J=1.34 Hz); 6.62 (tr, 1H, CH, J=8.2 Hz); 7.12 (dd, 1H, CH, J=8.2 Hz, J=2.55 Hz); 7.53 (s, 1H, CH pyr); 7.62 s, 1H, CH pyr).

Workup

  1. additionwere added under nitrogen atmosphere at room temperature
  2. customa consumption of the iodobenzene
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue purified by flash column chromatography (silica gel; dichloromethane:ethyl acetate 9:1)

Sources & evidence

ORD record
ord-28d9fbc1ba384e94b3604b7c73efc48c
Source dataset
uspto-grants-2013_10
Patent number
US08557982B2

Reaction notes

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