Diethylamine → HCID 86682928, compound

HRID 1497050Notes

Reaction equation

HRID 1497050 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4](I)[CH:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]#[CH:18].C(NCC)C>CN(C)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>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([C:18]#[C:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[Cl:10])[CH:3]=1

Participants

7

Reactant 3

HCID 8021DiethylamineHCID 5859951-Chloro-2-ethynylbenzeneHCID 27576154-Chloro-2-iodoaniline

Product 1

HCID 86682928HCID 86682928, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 4-chloro-2-iodo-phenylamine (500 mg, 1.97 mmol) in dimethylformamide (4 ml) was added PdCl2(PPh3)2 (7 mg, 0.02 mmol) followed by copper(I)iodide (3.7 mg, 0.02 mmol), 1-chloro-2-ethynyl-benzene (0.28 ml, 2.36 mmol) and diethylamine (1.65 ml, 15.78 mmol) under nitrogen at RT. The resulting reaction mixture was purged with nitrogen and then heated to 50° C. for 5 h. After cooling to room temperature, the mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo to give a crude residue which was purified by flash column chromatography (elution with 4% EtOAc in hexane) to yield 4-chloro-2-(2-chloro-phenylethynyl)-phenylamine (320 mg, 62% yield) as an off white solid. LC-MS: 262 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. customwas purged with nitrogen
  3. temperatureAfter cooling to room temperature
  4. additionthe mixture was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give a crude residue which
  10. customwas purified by flash column chromatography (elution with 4% EtOAc in hexane)

Sources & evidence

ORD record
ord-42a1ae943f494438b093acb08ce9ebcf
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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