3-(Methylsulfanyl)prop-1-yne → HCID 178503675, 화합물

HRID 2289982노트

반응식

HRID 2289982 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18](I)=[CH:17][C:16]=3[F:24])=[O:11])=[CH:4][CH:3]=1.[CH3:25][S:26][CH2:27][C:28]#[CH:29]>C(NCC)C.[Cu](I)I.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>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18]([C:29]#[C:28][CH2:27][S:26][CH3:25])=[CH:17][C:16]=3[F:24])=[O:11])=[CH:4][CH:3]=1

참가 물질

6

반응물 2

HCID 5254243-(Methylsulfanyl)prop-1-yne2회HCID 178522917HCID 178522917, 화합물

생성물 1

HCID 178503675HCID 178503675, 화합물

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8021Diethylamine용매

실험 절차

A mixture of N-[(4-Chlorophenyl)methyl]-8-fluoro-4-hydroxy-6-iodo-3-quinolinecarboxamide from Example No. 5 (1.57 g), propargyl methyl sulfide (0.355 g, 4.12 mmol), copper iodide (0.125 g), and dichlorobis(triphenylphosphine)palladium (II) (0.462 g) in diethylamine (38 mL) are stirred at room temperature overnight. An additional 0.092 g of propargyl methyl sulfide is added, and the mixture is stirred another 5 h. The reaction mixture was then concentrated in vacuo, and the residue is suspended in water (100 mL) and extracted with three portions of EtOAc. The combined organic layers are then dried over MgSO4, filtered, and concentrated in vacuo. Column chromatography (elution with 5-10%MeOH/CH2Cl2) yielded the title compound as a solid.

후처리

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. extractionextracted with three portions of EtOAc
  3. dry with materialThe combined organic layers are then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washColumn chromatography (elution with 5-10%MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-91bf0fe7c20948fc97ea09118ba37533
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06093732

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