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ChemicalBook CAS DataBase List diMethyl 2-(5-nitropyridin-2-yl)Malonate
68719-87-9

diMethyl 2-(5-nitropyridin-2-yl)Malonate synthesis

2synthesis methods
-

Yield:68719-87-9 95%

Reaction Conditions:

Stage #1: malonic acid dimethyl esterwith sodium hydride in tetrahydrofuran;1,4-dioxane; for 0.25 h;
Stage #2: 2-Fluoro-5-nitropyridine in tetrahydrofuran;1,4-dioxane;N,N-dimethyl-formamide;

Steps:

14.1

Example 14; Synthesis of 3-cyclopropyl-2-(5-(isopropylamino)pyridin-2-yl)-N-(4-(2-methylpyridin-4-yl)- phenyl)propanamide Step lTo a mixture of sodium hydride, 60% dispersion in mineral oil (1.8 g, 74 mmol) in THF (30 mL) and dioxane (20 mL) was added dimethyl malonate (8.4 ml, 74 mmol). The reaction mixture was stirred for 15 min, and a solution of 2-fluoro-5-nitropyridine (3.0 g, 21 mmol) in dioxane (10 mL) was added. The reaction mixture was added DMF (10 mL) and stirred overnight. 5N HCl was added to the mixture until pH 1 (40 mL). The reaction mixture was extracted with EtOAc and the organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (0%- 50% EtOAc-hexane) afforded dimethyl 2-(5-nitropyridin-2-yl)malonate as a yellow solid (5.1 g, 95%).

References:

WO2009/75874,2009,A1 Location in patent:Page/Page column 115-116