Toluene → HCID 67175166, 화합물

HRID 229412

반응식

HRID 229412 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[C:9]([C:11]1([NH2:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)#[CH:10].C(NC(C)C)(C)C.C1(C)C=CC=CC=1>C1COCC1.[Pt]=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)I>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:10][CH2:9][C:11]2([NH2:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:4][CH:3]=1

참가 물질

9

반응물 4

HCID 1140TolueneHCID 7912DiisopropylamineHCID 96054-FluoroiodobenzeneHCID 1216911-Ethynylcyclohexylamine

생성물 1

HCID 67175166HCID 67175166, 화합물

시약·촉매·용매 4

HCID 82844Platinum oxide (PtO)촉매HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

2.5 g (11.3 mmol) 1-fluoro-4-iodo-benzene, 1.5 g (11.9 mmol) 1-ethynyl-cyclohexylamine, 793 mg (1.13 mmol) PdCl2(PPh3)2, 67 mg (0.35 mmol) copper iodide and 50 mL diisopropylamine are stirred for 2 hours at 70° C. Then the base is distilled off and the residue is combined with ethyl acetate. The insoluble constituents are filtered off and the filtrate is evaporated down. The alkyne thus prepared is dissolved in 35 mL THF and 35 mL toluene and hydrogenated with platinum oxide as catalyst at normal pressure. The catalyst is separated off and the filtrate is freed from the solvent. The crude product is dissolved in ethyl acetate and combined with 10% hydrochloric acid in ethyl acetate. The precipitated solid is filtered off and washed with ethyl acetate. Yield: 1.3 g (45%; hydrochloride); mass spectroscopy: [M+H]+=222.

후처리

  1. distillationThen the base is distilled off
  2. filtrationThe insoluble constituents are filtered off
  3. customthe filtrate is evaporated down
  4. customThe alkyne thus prepared
  5. customThe catalyst is separated off
  6. dissolutionThe crude product is dissolved in ethyl acetate
  7. filtrationThe precipitated solid is filtered off
  8. washwashed with ethyl acetate

출처 및 근거

ORD 기록
ord-f636fad3df83406083af2ce852446265
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563806B2

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