Sodium hydride → Ethyl 2-(4-bromo-2-oxopyridin-1(2H)-yl)-3-cyclopropylpropanoate

HRID 56662

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.[CH:9]1([CH2:12][CH:13](OS(C)(=O)=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:11][CH2:10]1.[H-].[Na+].[Br-].[Li+]>>[Br:1][C:2]1[CH:7]=[CH:6][N:5]([CH:13]([CH2:12][CH:9]2[CH2:11][CH2:10]2)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:4](=[O:8])[CH:3]=1

Participants

Reactant 4

HCID 24758Sodium hydride

HCID 82050Lithium Bromide

HCID 8171154-Bromo-2-hydroxypyridine

HCID 117605475Ethyl 3-cyclopropyl-2-[(methylsulphonyl)oxy]propanoate

Product 1

HCID 117622870Ethyl 2-(4-bromo-2-oxopyridin-1(2H)-yl)-3-cyclopropylpropanoate

Conditions

Temperature: 65 °C

Procedure

1.02 g (5.87 mmol) of 4-bromopyridin-2(1H)-one and 2.23 g (purity 56%, 5.28 mmol) of ethyl 3-cyclopropyl-2-[(methylsulphonyl)oxy]propanoate (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 (stirred at 65° C. overnight). Yield: 246 mg (13% of theory)

Sources & evidence

ORD record: ord-e4b0243d8a54422bb0021d2b39bd193f
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434690B2

Linked notes

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