Toluene → HCID 67175166、化合物

HRID 229412

反応式

HRID 229412 の反応式
[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

参加物

9

反応物 4

HCID 1140TolueneHCID 7912DiisopropylamineHCID 96054-FluoroiodobenzeneHCID 1216911-Ethynylcyclohexylamine

生成物 1

HCID 67175166HCID 67175166、化合物

試薬・触媒・溶媒 4

HCID 82844Platinum oxide (PtO)触媒HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f636fad3df83406083af2ce852446265
出典データセット
uspto-grants-2009_07
特許番号
US07563806B2

関連ノート

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