Sodium hydride → HCID 89690441, compound

HRID 2202999Notes

Reaction equation

HRID 2202999 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[I:9][C:10]1[CH:11]=[CH:12][C:13]2[N:14]([C:16]([CH3:23])=[C:17](/[CH:19]=[CH:20]/[C:21]#[N:22])[N:18]=2)[CH:15]=1>CN(C=O)C>[I:9][C:10]1[CH:11]=[CH:12][C:13]2[N:14]([C:16]([CH3:23])=[C:17]([CH:19]3[CH2:4][CH:20]3[C:21]#[N:22])[N:18]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 89690613HCID 89690613, compound

Product 1

HCID 89690441HCID 89690441, compoundYield 6.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of NaH (60% in oil, 270 mg) in DMF (5 ml) was added trimethylsulfoxonium iodide (1.37 g) at room temperature, and the mixture was stirred for 3 h. A solution of (2E)-3-(6-iodo-3-methylimidazo[1,2-a]pyridin-2-yl)prop-2-enenitrile (600 mg) in DMF (1 ml) was added, and the resulting mixture was stirred at room temperature for 24 h. The reaction mixture was quenched with saturated NH4Cl solution and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, concentrated in vacuo, and purified by column chromatography (hexane/EtOAc) followed by preparative HPLC to afford the title compound (40 mg) as an off-white solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 24 h
  2. customThe reaction mixture was quenched with saturated NH4Cl solution
  3. extractionextracted with EtOAc
  4. washThe extract was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-2d3710059aa548ba991f7ca8f79364c6
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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