Sodium hydride → Ethyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-cyclobutylpropanoate

HRID 56819Notes

Reaction equation

HRID 56819 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+].[CH:21]1([CH2:25][CH:26](OS(C(F)(F)F)(=O)=O)[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:24][CH2:23][CH2:22]1>>[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:26]([CH2:25][CH:21]3[CH2:22][CH2:23][CH2:24]3)[C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:12](=[O:18])[CH:11]=2)[CH:3]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 1176049354-Chloro-2-(5-methoxy-2-oxo-1,2-dihydropyridin-4-yl)benzonitrileHCID 117605675Ethyl 3-cyclobutyl-2-{[(trifluoromethyl)sulphonyl]oxy}propanoate

Product 1

HCID 117622588Ethyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-cyclobutylpropanoate

Procedure

122 mg (purity 87%, 0.41 mmol) of 4-chloro-2-(5-methoxy-2-oxo-1,2-dihydropyridin-4-yl)benzonitrile in the presence of 1.3 eq. of sodium hydride and 161 mg (0.53 mmol, 1.3 eq.) of ethyl 3-cyclobutyl-2-{[(trifluoromethyl)sulphonyl]oxy}propanoate (racemate) were reacted at RT according to General 4E. The crude product was purified by flash chromatography (KP-SIL, cyclohexane/ethyl acetate 15-33%). Yield: 140 mg (82% of theory)

Workup

  1. customThe crude product was purified by flash chromatography (KP-SIL, cyclohexane/ethyl acetate 15-33%)

Sources & evidence

ORD record
ord-4b620418684b48efb6cf2942d20a4273
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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