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

HRID 1522633Notes

Reaction equation

HRID 1522633 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.Cl[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1>CN(C=O)C>[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[N:9][N:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:3]=12.[I:1][C:2]1[C:3]2[C:4](=[CH:8][N:9]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[N:10]=2)[N:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 699934-Methyloxybenzyl chlorideHCID 674695597-iodo-1H-pyrazolo[4,3-b]pyridine

Product 2

HCID 674695617-Iodo-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridineHCID 674704207-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 7-iodo-1H-pyrazolo[4,3-b]pyridine (500 mg, 2.041 mmol) in DMF (10 mL) at 0° C. was added 1-(chloromethyl)-4-methoxybenzene (0.292 mL, 2.143 mmol) and the reaction was allowed to warm to room temperature over 1 hour. The reaction mixture was then quenched with saturated ammonium chloride solution and extracted with ethyl acetate (50 mL×2). The organic layers were dried over sodium sulfate and concentrated to give a residue which was loaded onto silica and purified using a 0-77% gradient of ethyl acetate in hexanes to give 7-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridine and 7-iodo-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridine which was used immediately. MS [M+H] found 366.2.

Workup

  1. customThe reaction mixture was then quenched with saturated ammonium chloride solution
  2. extractionextracted with ethyl acetate (50 mL×2)
  3. dry with materialThe organic layers were dried over sodium sulfate
  4. concentrationconcentrated
  5. customto give a residue which
  6. custompurified

Sources & evidence

ORD record
ord-bb29535305254b1aa8d75f04d4075474
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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