Sodium hydride → HCID 117622794, compound

HRID 56901Notes

Reaction equation

HRID 56901 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][NH:13][C:12](=[O:18])[CH:11]=2)[CH:3]=1.[H-].[Na+].[CH3:21][CH:22]([CH3:37])[CH:23](OS(C(F)(F)F)(=O)=O)[C:24]([O:26][CH2:27][CH3:28])=[O:25]>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]2[C:15]([O:16][CH3:17])=[CH:14][N:13]([CH:23]([CH:22]([CH3:37])[CH3:21])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:12](=[O:18])[CH:11]=2)[CH:3]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 85433534HCID 85433534, compoundHCID 1176049354-Chloro-2-(5-methoxy-2-oxo-1,2-dihydropyridin-4-yl)benzonitrile

Product 1

HCID 117622794HCID 117622794, compound

Procedure

3.50 g (13.4 mmol) of 4-chloro-2-(5-methoxy-2-oxo-1,2-dihydropyridin-4-yl)benzonitrile in the presence of 1.5 eq. of sodium hydride and 5.60 g (20.1 mmol, 1.5 eq.) of ethyl 3-methyl-2-{[(trifluoromethyl)sulphonyl]oxy}butanoate (racemate) were reacted at RT according to General Method 4E. The crude product was purified by flash chromatography (silica gel 50, cyclohexane/ethyl acetate mixtures). Yield: 3.70 g (66% of theory)

Workup

  1. customThe crude product was purified by flash chromatography (silica gel 50, cyclohexane/ethyl acetate mixtures)

Sources & evidence

ORD record
ord-b05a79753aad4c7fa88d3400b2a7bcdf
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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