2-Bromopropane → 4-Chloro-3-iodo-1-(propan-2-yl)-1h-pyrazolo[4,3-c]pyridine

HRID 475020Notes

Reaction equation

HRID 475020 reaction equation
[Cl:1][C:2]1[C:7]2[C:8]([I:11])=[N:9][NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[H-].[Na+].Br[CH:15]([CH3:17])[CH3:16]>CN(C=O)C>[Cl:1][C:2]1[C:7]2[C:8]([I:11])=[N:9][N:10]([CH:15]([CH3:17])[CH3:16])[C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 178478341HCID 178478341, compound

Product 1

HCID 582092144-Chloro-3-iodo-1-(propan-2-yl)-1h-pyrazolo[4,3-c]pyridineYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine (103) (50 mg, 0.179 mmol) in DMF (1 mL) was cooled to 0° C., NaH (8.6 mg, 1.2 eq, 0.215 mmol) was added slowly and then 2-bromopropane was added dropwise. The solution was stirred overnight at room temperature. The mixture was concentrated in vacuo. The crude product was then purified by column chromatography using a gradient of CH2Cl2 in hexanes to afford 4-chloro-3-iodo-1-isopropyl-1H-pyrazolo[4,3-c]pyridine (301) (30 mg, 53% yield) as a white solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe crude product was then purified by column chromatography

Sources & evidence

ORD record
ord-df26489711b147f4bf153e72e4f70f71
Source dataset
uspto-grants-2014_01
Patent number
US08637542B2

Reaction notes

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