3-(Ethylsulfanyl)prop-1-yne → HCID 178477427, compound

HRID 2289983Notes

Reaction equation

HRID 2289983 reaction equation
[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.[CH2:25]([S:27][CH2:28][C:29]#[CH:30])[CH3:26]>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:30]#[C:29][CH2:28][S:27][CH2:25][CH3:26])=[CH:17][C:16]=3[F:24])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 5224803-(Ethylsulfanyl)prop-1-yneHCID 178522917HCID 178522917, compound

Product 1

HCID 178477427HCID 178477427, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Procedure

A mixture of N-[(4-chlorophenyl)methyl]-8-fluoro-4-hydroxy-6-iodo-3-quinolinecarboxamide from Example No. 5 (1.5 g), propargyl ethyl sulfide (1.04 g, 10.4 mmol), copper iodide (0.125 g), and dichlorobis(triphenylphosphine)-palladium(II) (0.462 g) in diethylamine are stirred at room temperature overnight. The reaction mixture is then concentrated in vacuo, and the residue is suspended in water (100 mL) and extracted with four 50-mL 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.

Workup

  1. concentrationThe reaction mixture is then concentrated in vacuo
  2. extractionextracted with four 50-mL 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)

Sources & evidence

ORD record
ord-70502929d2a84f5da1923bef6198c092
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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