Isopropyl iodide → 3-[5-(Benzyloxy)pyridin-2-yl]-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridine

HRID 573332Notes

Reaction equation

HRID 573332 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:19]3=[N:20][CH:21]=[CH:22][CH:23]=[C:18]3[NH:17][N:16]=2)=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].I[CH:31]([CH3:33])[CH3:32].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[C:19]3=[N:20][CH:21]=[CH:22][CH:23]=[C:18]3[N:17]([CH:31]([CH3:33])[CH3:32])[N:16]=2)=[N:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 667277533-[5-(Benzyloxy)pyridin-2-yl]-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 667278693-[5-(Benzyloxy)pyridin-2-yl]-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-[5-(benzyloxy)pyridin-2-yl]-1H-pyrazolo[4,3-b]pyridine (237 mg), K2CO3 (217 mg) in DMF (3 mL) was added 2-iodopropane (0.102 mL), and stirred at room temperature for 72 h. The mixture was poured into saturated NaHCO3 aqueous solution and extracted with AcOEt. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (219 mg).

Workup

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-0026827e683e414c95777e89f75b9782
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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