Diethyl (cyanomethyl)phosphonate → HCID 69184035, compound

HRID 2373234Notes

Reaction equation

HRID 2373234 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].CC(C)([O-])C.[K+].[CH2:18]([N:20]1[C:24]2=[N:25][C:26]([CH:43]=O)=[C:27]([CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[C:28]([C:29]3[CH:30]=[N:31][CH:32]=[C:33]([CH3:35])[CH:34]=3)=[C:23]2[CH:22]=[N:21]1)[CH3:19]>C1COCC1.O>[C:1](/[CH:3]=[CH:43]/[C:26]1[N:25]=[C:24]2[N:20]([CH2:18][CH3:19])[N:21]=[CH:22][C:23]2=[C:28]([C:29]2[CH:30]=[N:31][CH:32]=[C:33]([CH3:35])[CH:34]=2)[C:27]=1[CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])#[N:2]

Participants

6

Reactant 3

HCID 75676Diethyl (cyanomethyl)phosphonateHCID 23665647Potassium tert-butoxideHCID 86602412HCID 86602412, compound

Product 1

HCID 69184035HCID 69184035, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of diethyl (cyanomethyl)phosphonate (17.4 mg) in THF (0.5 ml) was added potassium tert-butoxide (11.3 mg) at 0° C. and the mixture was stirred at room temperature for 30 minutes. A solution of ethyl 3-[1-ethyl-6-formyl-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]propanoate (20 mg) in THF (0.5 ml) was added at 0° C. and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was washed with water, brine, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by preparative thin layer chromatography eluting with a mixture of EtOAc and n-hexane (1:1) to give ethyl 3-[6-[(E)-2-cyanovinyl]-1-ethyl-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]propanoate (17 mg) as a colorless crystal.

Workup

  1. stirringthe mixture was stirred at room temperature for 1.5 hours
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative thin layer chromatography
  7. washeluting with a mixture of EtOAc and n-hexane (1:1)

Sources & evidence

ORD record
ord-6d5b223178f24fd19aafc5807f9af4e2
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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