Sodium hydride → HCID 86668760, compound

HRID 533525Notes

Reaction equation

HRID 533525 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH2:5][S:6]([CH3:9])(=[O:8])=[O:7])[CH3:2].[H-].[Na+].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21]I)=[CH:16][N:15]=1.[Cl-].[NH4+]>CN(C=O)C>[Br:13][C:14]1[N:15]=[CH:16][C:17]([CH2:20][CH2:21][CH:5]([S:6]([CH3:9])(=[O:8])=[O:7])[C:4]([O:3][CH2:1][CH3:2])=[O:10])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 78201Ethyl methanesulfonylacetateHCID 866687632-Bromo-5-(2-iodoethyl)pyridine

Product 1

HCID 86668760HCID 86668760, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of ethyl(methylsulfonyl)acetate (1090 mg, 6.6 mmol, 1.0 equiv) in DMF (11 mL) was added dropwise to a mixture of 60% sodium hydride in mineral oil (315 mg, 7.9 mmol, 1.2 equiv) in DMF (11 mL) at 0° C. The reaction was warmed to room temperature and allowed to stir for 40 min. The reaction was cooled to 0° C. and a solution of 2-bromo-5-(2-iodoethyl)pyridine (2560 mg, 8.2 mmol, 1.3 equiv) in DMF (11 mL) was added dropwise, and the reaction was allowed to stir for 3 days. Saturated aqueous ammonium chloride solution (30 mL) was added, and the mixture was extracted with ethyl acetate (3×70 mL). The combined organic layers were washed with brine (60 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography (7:3 heptane/ethyl acetate) to provide the title compound as a white solid (1628 mg, 71%). MS (LCMS) m/z 352.1 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.29-1.35 (m, 3H) 2.30-2.44 (m, 2H) 2.62-2.78 (m, 2H) 3.00 (s, 3H) 3.71 (dd, J=9.37, 4.68 Hz, 1H) 4.21-4.35 (m, 2H) 7.36-7.46 (m, 2H) 8.19 (d, J=1.56 Hz, 1H).

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. stirringto stir for 3 days
  3. extractionthe mixture was extracted with ethyl acetate (3×70 mL)
  4. washThe combined organic layers were washed with brine (60 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by flash chromatography (7:3 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-95c6d38dd4cf4bed853a4c81deb69f6d
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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