Cesium carbonate → HCID 68816506, compound

HRID 1436601Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

Add methylpropylamine (0.21 mL, 2.0 mmol) to a suspension of 2-chloro-6-methanesulfonyl-isonicotinic acid methyl ester (0.25 g, 1.0 mmol), palladium acetate (0.022 g, 0.1 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.062 g, 0.1 mmol), and cesium carbonate (0.325 g, 1.0 mmol) in toluene (5 mL) at room temperature and stir 18 h at 80° C. Cool, filter through a filtering agent and purify (silica gel chromatography, eluting with 20:80 to 40:60 ethyl acetate:hexanes) to give the title compound (0.181 g, 63%).

Workup

temperatureCool
filtrationfilter through a filtering agent
custompurify
wash(silica gel chromatography, eluting with 20:80 to 40:60 ethyl acetate:hexanes)

Sources & evidence

ORD record: ord-aa78343b32ed46ec8e820e2172def4f1
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618978B2

Reaction notes

Loading…