Cesium carbonate → HCID 68814647, compound

HRID 1436580Notes

Reaction equation

HRID 1436580 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([S:10][CH2:11][CH2:12][CH3:13])[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+].[C@@H:68]([NH2:72])([CH2:70][CH3:71])[CH3:69]>CCOCC.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([S:10][CH2:11][CH2:12][CH3:13])[N:7]=[C:6]([NH:72][CH:68]([CH2:70][CH3:71])[CH3:69])[CH:5]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 67137532-Butanamine, (S)-HCID 86081340HCID 86081340, compound

Product 1

HCID 68814647HCID 68814647, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

Add 2-chloro-6-propylsulfanyl-isonicotinic acid methyl ester (1.35 g, 5.49 mmol) palladium acetate (0.123 g, 0.549 mmol, 0.1eq.), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.342 g, 0.549 mmol, 0.1 eq.), cesium carbonate (2.68 g, 8.24 mmol, 1.5 eq.) and toluene (20 mL) into a sealed vessel flushed with nitrogen. Slowly add (S)-sec-butylamine (0.824 mL, 8.24 mmol) and heat and stir the reaction mixture at 90° C. for 18 h. Cool the reaction mixture to room temperature, dilute with ether and filter through a filtering agent. Concentrate the filtrate and purify (silica gel chromatography, eluting with the 5:95 to 10:90 ethyl acetate:hexanes) to give the title compound (55%).

Workup

  1. customflushed with nitrogen
  2. temperatureCool the reaction mixture to room temperature
  3. filtrationfilter through a filtering agent
  4. concentrationConcentrate the filtrate
  5. custompurify (silica gel chromatography
  6. washeluting with the 5:95 to 10:90 ethyl acetate

Sources & evidence

ORD record
ord-199b3c65ef0a40f3ad0bdca6ebac75e4
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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