Iodine → HCID 178452207, compound

HRID 387528Notes

Reaction equation

HRID 387528 reaction equation
[CH:1]1([C:4]2[C:5]([N:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)=[C:6]3[CH:12]=[N:11][NH:10][C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[OH-].[K+].[I:28]I>CN(C=O)C.CCOC(C)=O>[CH:1]1([C:4]2[C:5]([N:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)=[C:6]3[C:12]([I:28])=[N:11][NH:10][C:7]3=[N:8][CH:9]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 68757650tert-butyl 4-(5-cyclopropyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

Product 1

HCID 178452207HCID 178452207, compoundYield 102.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of tert-butyl 4-(5-cyclopropyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (1.44 g, 4.19 mmol) and powdered potassium hydroxide (0.692 g, 10.5 mmol) in DMF (20 mL) was treated with iodine (2.13 g, 8.39 mmol), and the mixture was heated at 60° C. for 5 hours. The mixture was diluted with EtOAc (200 mL) and successively washed with saturated Na2S2O3 solution (2×20 mL) and water (2×50 mL). The organic layer was separated, dried (MgSO4), filtered, and concentrated in vacuo to provide the crude tert-butyl 4-(5-cyclopropyl-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (2.01 g, 4.28 mmol, 100%) yield) as a solid.

Workup

  1. washsuccessively washed with saturated Na2S2O3 solution (2×20 mL) and water (2×50 mL)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f3bc867ec91e4ef89df6837bdfd1d474
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

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