Propyl mercaptan → HCID 86081340, compound

HRID 732416Notes

Reaction equation

HRID 732416 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=[C:6](Cl)[CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:65]([SH:68])[CH2:66][CH3:67]>C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:5]=[C:6]([S:68][CH2:65][CH2:66][CH3:67])[N:7]=[C:8]([Cl:10])[CH:9]=1

Participants

8

Reactant 4

HCID 7848Propyl mercaptanHCID 10796Cesium carbonateHCID 93237Methyl 2,6-dichloroisonicotinateHCID 634876Binap, (A+-)-

Product 1

HCID 86081340HCID 86081340, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

Add 2,6-dichloroisonicotinic acid methyl ester (4.12 g, 20.0 mmol), toluene (40 mL), palladium acetate (448 mg, 2.0 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.25 g, 2.0 mmol) and cesium carbonate (7.82 g, 24.0 mmol) into a sealed vessel flushed with nitrogen. Slowly add propanethiol (2.2 mL, 24 mmol). Heat and stir the reaction mixture at 80° C. for 18 h. Cool to room temperature, dilute with diethyl ether and filter through a filtering agent. Concentrate the filtrate and purify (silica gel chromatography, 2:98 to 5:95 ethyl acetate:hexane) to give the title compound (55%).

Workup

  1. customflushed with nitrogen
  2. temperatureHeat
  3. temperatureCool to room temperature
  4. filtrationfilter through a filtering agent
  5. concentrationConcentrate the filtrate
  6. custompurify (silica gel chromatography, 2:98 to 5:95 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-1218d37846504b3686fd48822668afda
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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