3-(Methylsulfanyl)prop-1-yne → HCID 178503675、化合物

HRID 2289982ノート

反応式

HRID 2289982 の反応式
[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

参加物

6

反応物 2

HCID 5254243-(Methylsulfanyl)prop-1-yne2 回HCID 178522917HCID 178522917、化合物

生成物 1

HCID 178503675HCID 178503675、化合物

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 8021Diethylamine溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-91bf0fe7c20948fc97ea09118ba37533
出典データセット
uspto-grants-2000_07
特許番号
US06093732

反応ノート

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