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

HRID 2289982Notes

Reaction equation

HRID 2289982 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.[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

Participants

6

Reactant 2

HCID 5254243-(Methylsulfanyl)prop-1-yne2×HCID 178522917HCID 178522917, compound

Product 1

HCID 178503675HCID 178503675, 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 (1.57 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.

Workup

  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)

Sources & evidence

ORD record
ord-91bf0fe7c20948fc97ea09118ba37533
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

Loading…