Sodium hydride → HCID 57742059, compound

HRID 1880000Notes

Reaction equation

HRID 1880000 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:18])([CH2:9][O:10][C:11]1[C:12]([NH2:17])=[N:13][CH:14]=[CH:15][CH:16]=1)[C:5](OC)=[O:6]>CS(C)=O.O>[CH3:3][C:4]1([CH3:18])[CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[N:13][C:12]=2[NH:17][C:5]1=[O:6]

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 57742044HCID 57742044, compound

Product 1

HCID 57742059HCID 57742059, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

NaH (60% in oil 533 mg) was added to a solution of methyl 2,2-dimethyl-3-(2-aminopyridin-3-yloxy)propanoate (8.04, 37 mmol) in DMSO (400 mL) and the mixture stirred overnight at rt. The mixture was diluted with water and separated. The aqueous layer was washed with ethyl acetate and the combined organic phases were dried over magnesium sulfate and evaporated in vacuo to afford the title compound (6.5 g, 94%). 1H NMR (300 MHz, DMSO-d6) δ 9.83 (s, 1H), 7.96 (d, J=4.0 Hz, 1H), 7.37 (d, J=8.0 Hz, 1H), 6.98 (m, 1H), 4.02 (s, 2H), 1.47 (s, 6H)

Workup

  1. customseparated
  2. washThe aqueous layer was washed with ethyl acetate
  3. dry with materialthe combined organic phases were dried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-8090e39e54964f9fadc869f13336d53c
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

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