Isopropyl iodide → 7-iodo-2-isopropyl-2H-pyrazolo[4,3-b]pyridine

HRID 1522605Notes

Reaction equation

HRID 1522605 reaction equation
[I:1][C:2]1[C:3]2[C:4](=[CH:8][NH:9][N:10]=2)[N:5]=[CH:6][CH:7]=1.I[CH:12]([CH3:14])[CH3:13].[H-].[Na+]>CN(C=O)C.O.C(#N)C.O>[I:1][C:2]1[C:3]2[C:4](=[CH:8][N:9]([CH:12]([CH3:14])[CH3:13])[N:10]=2)[N:5]=[CH:6][CH:7]=1.[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[N:9][N:10]([CH:12]([CH3:14])[CH3:13])[C:3]=12

Participants

8

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 178506553HCID 178506553, compound

Product 2

HCID 674695507-iodo-2-isopropyl-2H-pyrazolo[4,3-b]pyridineYield 29.9%HCID 674704007-iodo-1-isopropyl-1H-pyrazolo[4,3-b]pyridineYield 0.34%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

7-Iodo-2H-pyrazolo[4,3-b]pyridine (100 mg, 0.408 mmol), 2-iodopropane (0.049 ml, 0.490 mmol) and sodium hydride (19.59 mg, 0.816 mmol) were combined in DMF (5 mL). The mixture was stirred at room temperature for 1 hour then quenched by the addition of ice. The reaction mixture was purified by preparative HPLC eluting with a gradient of 20-90% 10 mmol NH4HCO3 in 20/80 (v/v) water/acetonitrile in 10 mmol NH4HCO3 in water using a Phenomenex Gemini Prep 5 μm C18, 75×30 mm column to give 7-iodo-2-isopropyl-2H-pyrazolo[4,3-b]pyridine (35 mg, 29.9% yield) and 7-iodo-1-isopropyl-1H-pyrazolo[4,3-b]pyridine (25 mg, 0.34% yield). MS [M+H] found 288.1.

Workup

  1. customthen quenched by the addition of ice
  2. customThe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-c395908f05bc4e5fa1c6b71a711fbf0f
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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