Diethylamine → HCID 86682928, 화합물

HRID 1497050노트

반응식

HRID 1497050 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

HCID 86682928HCID 86682928, 화합물수율 62%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-42a1ae943f494438b093acb08ce9ebcf
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199938B2

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