Sodium hydride → 7-Iodo-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridine

HRID 1522601Notes

Reaction equation

HRID 1522601 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.[H-].[Na+].Cl[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1>CN(C=O)C.O.C(#N)C.O>[I:1][C:2]1[C:3]2[C:4](=[CH:8][N:9]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[N:10]=2)[N:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 178506553HCID 178506553, compound

Product 1

HCID 674695617-Iodo-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridineYield 20.1%

Reagents, catalysts & solvents 3

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

Procedure

7-Iodo-2H-pyrazolo[4,3-b]pyridine (1 g, 4.08 mmol) and sodium hydride (0.196 g, 8.16 mmol) were combined in DMF (15 mL) at room temperature. The mixture was stirred at room temperature for 10 minutes and 1-(chloromethyl)-4-methoxybenzene (0.554 ml, 4.08 mmol) was added. The mixture was stirred at room temperature for 1 hour the quenched with ice water and purified by preparative HPLC using a Phenomenex Gemini Prep 5 μm C18, 75×30 mm column eluting with a gradient of 20-90% 10 mmol NH4HCO3 in 20/80 (v/v) water/acetonitrile in 10 mmol NH4HCO3 in water to give the 7-iodo-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridine (300 mg, 20.1% yield) as a white powder. MS [M+H] found 366.1.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour the
  2. customquenched with ice water
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-f42cffc50f3546db991179c615b2bc8a
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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