Cesium carbonate → HCID 68814257, compound

HRID 732423Notes

Reaction equation

[C:1]([O:5][C:6](=[O:20])[C:7]1[CH:12]=[C:11]([S:13]([CH:16]2[CH2:18][CH2:17]2)(=[O:15])=[O:14])[N:10]=[C:9](Cl)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].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:73]([NH2:77])([CH2:75][CH3:76])C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6](=[O:20])[C:7]1[CH:12]=[C:11]([S:13]([CH:16]2[CH2:18][CH2:17]2)(=[O:15])=[O:14])[N:10]=[C:9]([NH:77][CH:73]2[CH2:76][CH2:75]2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

Add 2-chloro-6-cyclopropanesulfonyl-isonicotinic acid tert-butyl ester (0.190 g, 0.607 mmol), palladium acetate (0.020 g, 0.091 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.057 g, 0.091 mmol), cesium carbonate (0.297 g, 0.911 mmol), and (S)-sec-butylamine (0.063 mL, 0.911 mmol) in toluene (5 mL) to a sealed tube flushed with nitrogen. Heat and stir the reaction mixture at 90° C. for 18 h. Cool and filter the mixture through a pad of filtering agent, concentrate and purify (silica gel chromatography, eluting with 20:80 ethyl acetate:hexanes) to give the title compound (0.120 g, 59%).

Workup

customflushed with nitrogen
temperatureHeat
temperatureCool
filtrationfilter the mixture through a pad
filtrationof filtering agent
concentrationconcentrate
custompurify
wash(silica gel chromatography, eluting with 20:80 ethyl acetate:hexanes)

Sources & evidence

ORD record: ord-b71e9c77eaf641c28ae1c3d2d681020c
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585885B2

Reaction notes

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