Triethylamine → HCID 24952433, compound

HRID 391513Notes

Reaction equation

HRID 391513 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:19]=1)[C:7]([N:9]=[S@@:10]([CH3:18])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[F:28])#[CH:21].C(N(CC)CC)C>CCOC(C)=O.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>[F:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:20]#[C:21][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:19]=1)[C:7]([N:9]=[S@@:10]([CH3:18])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 6433581-Ethynyl-2-fluorobenzeneHCID 86629466(S)-5-bromo-N-[methyl(oxido)phenyl--sulfanylidene]nicotinamide

Product 1

HCID 24952433HCID 24952433, compoundYield 94%

Reagents, catalysts & solvents 3

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

Procedure

A mixture of (S)-5-bromo-N-[methyl(oxo)phenyl-λ6-sulfanylidene]nicotinamide (105 mg, 0.31 mmol) and 1-ethynyl-2-fluorobenzene (75 mg, 0.62 mmol) in 2.0 mL EtOAc was degassed with argon at 70° C. Upon cooling to room temperature the reaction mixture was treated with triethylamine (0.16 mL, 1.1 mmol), dichlorobis(triphenylphosphine)palladium(II) (22 mg, 0.031 mmol) and copper(I) iodide (2 mg, 0.012 mmol). The reaction was heated at 70° C. for 20 hours then partitioned between EtOAc and H2O. The EtOAc layer was washed with acetic acid solution, saturated NaHCO3, brine, dried with anhydrous Na2SO4 and concentrated. The dark film obtained was purified by chromatography (silica gel, hexane/EtOAc) to give the title compound as a tan foam (110 mg, 94%).

Workup

  1. customwas degassed with argon at 70° C
  2. temperatureThe reaction was heated at 70° C. for 20 hours
  3. customthen partitioned between EtOAc and H2O
  4. washThe EtOAc layer was washed with acetic acid solution, saturated NaHCO3, brine
  5. dry with materialdried with anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe dark film obtained
  8. customwas purified by chromatography (silica gel, hexane/EtOAc)

Sources & evidence

ORD record
ord-8004965daedf4431b13bed6fe6c84856
Source dataset
uspto-grants-2013_02
Patent number
US08383825B2

Reaction notes

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