Triethylamine → HCID 57961823, compound

HRID 541570Notes

Reaction equation

HRID 541570 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])=[C:4]([N+:14]([O-:16])=[O:15])[CH:3]=1.C(N(CC)CC)C.[C:24]([C:26]1[CH:27]=[C:28]([CH:30]=[CH:31][CH:32]=1)[NH2:29])#[CH:25]>O1CCCC1.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>[CH:11]([S:8]([C:5]1[CH:6]=[CH:7][C:2]([C:25]#[C:24][C:26]2[CH:27]=[C:28]([CH:30]=[CH:31][CH:32]=2)[NH2:29])=[CH:3][C:4]=1[N+:14]([O-:16])=[O:15])(=[O:10])=[O:9])([CH3:13])[CH3:12]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 104682Benzenamine, 3-ethynyl-HCID 56945987HCID 56945987, compound

Product 1

HCID 57961823HCID 57961823, compoundYield 72.6%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Bromo-1-(isopropylsulfonyl)-2-nitrobenzene (390 mg, 1.3 mmol), bis(triphenylphosphine)palladium(II) chloride (60 mg, 0.08 mmol) and copper(I) iodide (20 mg, 0.1 mmol) were stirred in tetrahydrofuran (5 mL) with triethylamine (250 μL, 1.8 mmol). 3-Ethynylaniline (100 μL, 1.0 mmol) was added and the mixture was stirred at rt for 1.5 hours. The mixture was evaporated, diluted with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The extracts were dried over sodium sulfate, filtered and evaporated to give the desired compound (250 mg, 60%). LCMS for C17H17N2O4S (M+H)+: m/z=345.1.

Workup

  1. customThe mixture was evaporated
  2. additiondiluted with saturated aqueous sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-5f23c327aa1d42439b9e9003f72c7df4
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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