Triethylamine → 3-(3,4-Difluoro-phenylethynyl)-phenylamine

HRID 1030867

반응식

HRID 1030867 반응식
[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[CH:6][C:7]=1[F:8].C(N(CC)CC)C.[NH2:17][C:18]1[CH:19]=[C:20]([C:24]#[CH:25])[CH:21]=[CH:22][CH:23]=1>CCOCC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:25]#[C:24][C:20]2[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=2)[NH2:17])[CH:5]=[CH:6][C:7]=1[F:8]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 676754-Bromo-1,2-difluorobenzeneHCID 104682Benzenamine, 3-ethynyl-

생성물 1

HCID 198210783-(3,4-Difluoro-phenylethynyl)-phenylamine수율 38.5%

시약·촉매·용매 3

HCID 11776Triphenylphosphine촉매HCID 10122028Bis(triphenylphosphine)palladium촉매HCID 3283Diethyl Ether용매

반응 조건

온도
65 °C

실험 절차

A multinecked flask as described in Example 1 was charged with 5.0 g (0.026 mol) of 3,4-difluorobromobenzene, 50 ml of dried, degassed triethylamine, 3.0 g (0.026 mol) of 3-aminophenylacetylene, 0.07 g (0.1 mmol) of bis(triphenylphosphine) palladium II chloride, 0.1 g (0.38 mmol) of triphenylphosphine, and 0.02 g (0.1 mmol) of cuprous iodide. The reaction mixture was heated at 65° C. for 36 hours at which point gas chromatography showed the reaction to be complete. The product mixture was cooled to room temperature and diluted with 50 ml of ether. Filtration of the insoluble triethylamine hydrobromide salt by-product followed by concentration of the filtrate gave the crude product (4.2 g, 78% yield) as a off-white solid. Short path distillation of the crude product under reduced pressure gave 2.38 g (0.01 mol, 38% yield) of the purified product as a colorless liquid which crystallized on standing.

후처리

  1. customA multinecked flask as described in Example 1
  2. customof dried
  3. customthe reaction
  4. temperatureThe product mixture was cooled to room temperature
  5. filtrationFiltration of the insoluble triethylamine hydrobromide salt by-product
  6. customgave the crude product (4.2 g, 78% yield) as a off-white solid
  7. distillationShort path distillation of the crude product under reduced pressure

출처 및 근거

ORD 기록
ord-a47d3c9b012e4946870460f490c5eda2
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05107026

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