Sodium hydride → Ethyl 2-(4-iodo-2-oxopyridin-1(2H)-yl)hexanoate

HRID 56657Notes

Reaction equation

[I:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.Br[CH:10]([CH2:16][CH2:17][CH2:18][CH3:19])[C:11]([O:13][CH2:14][CH3:15])=[O:12].[H-].[Na+].[Br-].[Li+]>>[I:1][C:2]1[CH:7]=[CH:6][N:5]([CH:10]([CH2:16][CH2:17][CH2:18][CH3:19])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:4](=[O:8])[CH:3]=1

Participants

Reactant 4

HCID 24758Sodium hydride

HCID 79072Ethyl 2-bromohexanoate

HCID 82050Lithium Bromide

HCID 205825354-Iodo-1,2-dihydropyridin-2-one

Product 1

HCID 117622881Ethyl 2-(4-iodo-2-oxopyridin-1(2H)-yl)hexanoate

Procedure

500 mg (2.3 mmol) of 4-iodopyridin-2(1H)-one and 706 mg (3.2 mmol) of ethyl 2-bromohexanoate (racemate) in the presence of 1.15 eq. of sodium hydride and 2.3 eq. of lithium bromide were reacted according to General Method 4C. Yield: 352 mg (43% of theory)

Sources & evidence

ORD record: ord-e224993d741441e4a7233bc3c8509374
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434690B2

Reaction notes

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