Cesium carbonate → (S)-2-sec-Butylamino-6-methylsulfanyl-isonicotinic acid methyl ester

HRID 732414Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8](Cl)[N:7]=[C:6]([NH:11][C@H:12]([CH2:14][CH3:15])[CH3:13])[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+].[CH3:69][S-:70].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([S:70][CH3:69])[N:7]=[C:6]([NH:11][C@H:12]([CH2:14][CH3:15])[CH3:13])[CH:5]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Add toluene (20 mL), (S)-2-sec-butylamino-6-chloro-isonicotinic acid methyl ester (2.01 g, 8.29 mmol), palladium acetate (186 mg, 0.83 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (516 mg, 0.83 mmol), cesium carbonate (5.40 g, 16.6 mmol), and sodium thiomethoxide (1.16 g, 16.6 mmol) to a sealed vessel flushed with nitrogen. Heat the sealed vessel at 90° C. overnight. Cool to room temperature and filter the solution through a filtering agent and concentrate the filtrate. Purify the residue (silica gel chromatography, eluting with ethyl acetate:hexanes 90:10) to give the title compound (1.4 g, 66%).

Workup

customflushed with nitrogen
temperatureCool to room temperature
filtrationfilter the solution through a filtering agent
concentrationconcentrate the filtrate
customPurify
washthe residue (silica gel chromatography, eluting with ethyl acetate:hexanes 90:10)

Sources & evidence

ORD record: ord-82555d2f395f434886aaa54dad42b379
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585885B2

Reaction notes

Loading…