Sodium hydride → HCID 57527167, compound

HRID 1671796Notes

Reaction equation

HRID 1671796 reaction equation
[NH2:1][C:2]1[C:12](Br)=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1.[CH:14]([N:17]=[C:18]=[S:19])([CH3:16])[CH3:15].[H-].[Na+].CCOC(C)=O.CCCCCC>CN(C=O)C>[CH:14]([NH:17][C:18]1[S:19][C:12]2[C:2]([N:1]=1)=[N:3][CH:4]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:11]=2)([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 75263Isopropyl IsothiocyanateHCID 7210833Ethyl 6-amino-5-bromonicotinateHCID 21226206Ethyl acetate hexane

Product 1

HCID 57527167HCID 57527167, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of ethyl 6-amino-5-bromonicotinate (0.780 g, 3.18 mmol) and isopropyl isothiocyanate (0.34 mL, 3.19 mmol) in DMF (8 mL) was added sodium hydride (60% oil dispersion) at 0° C. in one portion. The mixture was heated at 65° C. for 20 hr, and then at 75° C. for 40 hr. After it cooled to rt, the reaction was quenched with 1N HCl (5 mL). The mixture was poured into saturated NaHCO3 solution and extracted with AcOEt (3×40 mL). The combined extract was washed with 10% lithium chloride solution (2×30 mL) and dried over anhydrous MgSO4. The title compound (0.291 g, 34% yield) was isolated as a white solid by flash chromatography (60% AcOEt/hexane).

Workup

  1. temperatureAfter it cooled to rt
  2. customthe reaction was quenched with 1N HCl (5 mL)
  3. additionThe mixture was poured into saturated NaHCO3 solution
  4. extractionextracted with AcOEt (3×40 mL)
  5. extractionThe combined extract
  6. washwas washed with 10% lithium chloride solution (2×30 mL)
  7. dry with materialdried over anhydrous MgSO4

Sources & evidence

ORD record
ord-681cb94b922141fe975481b235277755
Source dataset
uspto-grants-2011_08
Patent number
US07994337B2

Reaction notes

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