Triethylamine → 1-{2-[(3-Aminophenyl)ethynyl]phenyl}urea

HRID 530428Notes

Reaction equation

HRID 530428 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH2:11])=[O:10].[C:12]([C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17])#[CH:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C.[Cu]I.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>[NH2:17][C:16]1[CH:15]=[C:14]([C:12]#[C:13][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[NH:8][C:9]([NH2:11])=[O:10])[CH:20]=[CH:19][CH:18]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 104682Benzenamine, 3-ethynyl-HCID 139387Urea, (2-iodophenyl)-

Product 1

HCID 1212546291-{2-[(3-Aminophenyl)ethynyl]phenyl}urea

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the nitrogen degassed solution of 1-(2-iodophenyl)urea (1.31 g, 5 mmol, 1 eq), 3-ethynylaniline (0.8 mL, 1.5 eq), triphenylphosphine (32.8 mg, 0.025 eq), and triethylamine (2.1 mL, 3 eq) in anhydrous DMF (12.5 mL) was added copper(I) iodide (190.4 mg, 0.2 eq) and bis(triphenylphosphine)palladium(II) dichloride (351 mg, 0.1 eq). After the reaction mixture was stirred at room temperature for 10 minutes, it was diluted with ethyl acetate, washed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, brine, and lastly dried with anhydrous sodium sulfate. The upper solution was decanted, concentrated, and the solid mixture was subject to a gradient column chromatography (EtOAc-Hex 1:2 to MeOH-EtOAc 1:9) to give 1-{2-[(3-aminophenyl)ethynyl]phenyl}urea as a brown solid in amount of 1.26 g.

Workup

  1. washwashed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, brine
  2. dry with materiallastly dried with anhydrous sodium sulfate
  3. customThe upper solution was decanted
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-04637a0d363e4c53acfb0a02963fd6b2
Source dataset
uspto-grants-2016_05
Patent number
US09353093B2

Reaction notes

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