Sodium hydride → tert-butyl 4-((7-iodo-2H-pyrazolo[4,3-b]pyridin-2-yl)methyl)piperidine-1-carboxylate

HRID 1522586Notes

Reaction equation

HRID 1522586 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[N:9][NH:10][C:3]=12.[H-].[Na+].[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([CH2:26]Br)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>CN(C=O)C>[I:1][C:2]1[C:3]2[C:4](=[CH:8][N:9]([CH2:26][CH:23]3[CH2:24][CH2:25][N:20]([C:18]([O:17][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:19])[CH2:21][CH2:22]3)[N:10]=2)[N:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylateHCID 674695597-iodo-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 67469653tert-butyl 4-((7-iodo-2H-pyrazolo[4,3-b]pyridin-2-yl)methyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7-iodo-1H-pyrazolo[4,3-b]pyridine (76 mg, 0.310 mmol) in DMF (4 ml) was cooled in an ice bath. Sodium hydride (16.13 mg, 0.403 mmol) was added and the reaction was stirred for 5 minutes. 4-Bromomethyl-piperidine-1-carboxylic acid tert-butyl ester (104 mg, 0.372 mmol) was added and the reaction was warmed to room temperature and then to 65° C. for 20 minutes. The reaction was then cooled, quenched with water and saturated NH4Cl solution and extracted with EtOAc. The organic layer were separated, dried over Na2SO4, filtered, and concentrated in vacuo to give tert-butyl 4-((7-iodo-2H-pyrazolo[4,3-b]pyridin-2-yl)methyl)piperidine-1-carboxylate which was used in the next step without further purification.

Workup

  1. waitto 65° C. for 20 minutes
  2. temperatureThe reaction was then cooled
  3. customquenched with water and saturated NH4Cl solution
  4. extractionextracted with EtOAc
  5. customThe organic layer were separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d79fb6a94c4b47ea87a727a66a7db266
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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