Sodium hydride → HCID 89690613, compound

HRID 2202998Notes

Reaction equation

HRID 2202998 reaction equation
C(OP([CH2:9][C:10]#[N:11])(=O)OCC)C.[H-].[Na+].[I:14][C:15]1[CH:16]=[CH:17][C:18]2[N:19]([C:21]([CH3:26])=[C:22]([CH:24]=O)[N:23]=2)[CH:20]=1>C1COCC1>[I:14][C:15]1[CH:16]=[CH:17][C:18]2[N:19]([C:21]([CH3:26])=[C:22](/[CH:24]=[CH:9]/[C:10]#[N:11])[N:23]=2)[CH:20]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 89690255HCID 89690255, compound

Product 1

HCID 89690613HCID 89690613, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of cyanomethylphosphonic acid diethyl ester (619 mg) in THF (2 ml) was added NaH (60% in oil, 144 mg) at 0° C., and the mixture was stirred at same temperature for 16 h. A solution of 6-iodo-3-methylimidazo[1,2-a]pyridine-2-carbaldehyde (250 mg) in THF (2 ml) was added, and the resulting mixture was stirred at room temperature for 4 h. The reaction mixture was quenched with saturated NH4Cl solution, and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, concentrate, and purified by column chromatography (hexane/EtOAc) to afford the title compound (120 mg) as a pale yellow solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 4 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. concentrationconcentrate
  7. custompurified by column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-2baa6132971b4d77a2cf092ce46e8209
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

Loading…