Benzyl Bromide → benzyl 1-benzyl-6-chloro-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

HRID 574993Notes

Reaction equation

HRID 574993 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([N:16]1[C:20]2[N:21]=[C:22]([Cl:28])[CH:23]=[C:24]([C:25]([OH:27])=[O:26])[C:19]=2[CH:18]=[N:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:9]([N:16]1[C:20]2[N:21]=[C:22]([Cl:28])[CH:23]=[C:24]([C:25]([O:27][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:26])[C:19]=2[CH:18]=[N:17]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1177780091-benzyl-6-chloro-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 117778156benzyl 1-benzyl-6-chloro-1H-pyrazolo[3,4-b]pyridine-4-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (11 mL/89 mol) is added dropwise to a suspension of 1-benzyl-6-chloro-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (27.0 g/93.9 mmol) and potassium carbonate (15.6 g/112 mmol) in 310 mL of DMF. The mixture is stirred at ambient temperature for 2 hours and then run into a saturated aqueous solution of ice-cold NaHCO3. The precipitate formed is filtered, thoroughly washed with water, and dried under vacuum to give 32.6 g of a pale yellow powder (yield: 92%).

Workup

  1. customThe precipitate formed
  2. filtrationis filtered
  3. washthoroughly washed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-51fbcd700a84434f9fdc3a509c9d90f8
Source dataset
uspto-grants-2015_05
Patent number
US09034898B2

Reaction notes

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