Iodoethane → 3-[5-(Benzyloxy)pyridin-2-yl]-1-ethyl-1H-pyrazolo[4,3-b]pyridine

HRID 573324Notes

Reaction equation

HRID 573324 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[C:25]3=[N:26][CH:27]=[CH:28][CH:29]=[C:24]3[NH:23][N:22]=2)=[N:19][CH:20]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:30](I)[CH3:31].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[C:25]3=[N:26][CH:27]=[CH:28][CH:29]=[C:24]3[N:23]([CH2:30][CH3:31])[N:22]=2)=[N:19][CH:20]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 667277533-[5-(Benzyloxy)pyridin-2-yl]-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 667280313-[5-(Benzyloxy)pyridin-2-yl]-1-ethyl-1H-pyrazolo[4,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of K2CO3 (212 mg, 1.53 mmol), 3-[5-(benzyloxy)pyridin-2-yl]-1H-pyrazolo[4,3-b]pyridine (232 mg) in DMF (3 mL) was added EtI (0.064 mL), and stirred at room temperature overnight. The mixture was added to saturated NaHCO3 aqueous solution and extracted with AcOEt. The organic layer was separated, washed with brine and dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (224 mg).

Workup

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-134e55d5e8524d95b8017e93e2534d8d
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

Loading…