Iodine → HCID 178490906, compound

HRID 387589

Reaction equation

HRID 387589 reaction equation
[I:1]I.[CH3:3][O:4][C:5]1[CH:21]=[CH:20][C:8]([CH2:9][N:10]2[C:14]3[N:15]=[CH:16][CH:17]=[C:18]([OH:19])[C:13]=3[CH:12]=[N:11]2)=[CH:7][CH:6]=1.C(=O)(O)[O-].[Na+].OS([O-])(=O)=O.[K+]>C(O)C>[I:1][C:17]1[CH:16]=[N:15][C:14]2[N:10]([CH2:9][C:8]3[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:21][CH:20]=3)[N:11]=[CH:12][C:13]=2[C:18]=1[OH:19]

Participants

6

Reactant 4

HCID 807IodineHCID 516892Sodium BicarbonateHCID 516920Potassium bisulfateHCID 178490904HCID 178490904, compound

Product 1

HCID 178490906HCID 178490906, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

Diiodine (0.547 g, 2.16 mmol) in ethanol (5 mL) was added dropwise over 5 minutes to a solution of 1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-ol (0.50 g, 1.96 mmol, prepared similarly as that described in WO 2007/103308) in absolute ethanol (20 mL) at 0° C. The reaction was stirred at 0° C. for 3 hours, followed by addition of 5% sodium bicarbonate (20 mL). The mixture was concentrated to give a slurry. The pH was then adjusted with saturated KHSO4 to a pH of 4. The resulting solid was collected by filtration and dried to give 5-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-ol (0.70 g, 94%). MS APCI (+) m/z 382.0 detected.

Workup

  1. customprepared similarly as
  2. customat 0° C
  3. concentrationThe mixture was concentrated
  4. customto give a slurry
  5. filtrationThe resulting solid was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-526f04bf4ae94df5a13eaf4fe84dee0b
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Linked notes

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