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Iodine → HCID 178452246, compound

HRID 387569
Notes
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Reaction equation

HRID 387569 reaction equation
[I:1]I.[NH:3]1[C:7]2=[N:8][CH:9]=[CH:10][C:11]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)=[C:6]2[CH:5]=[N:4]1.[OH-].[K+].[O-]S([O-])=O.[Na+].[Na+]>CN(C=O)C.CCOCC>[I:1][C:5]1[C:6]2[C:7](=[N:8][CH:9]=[CH:10][C:11]=2[N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)[NH:3][N:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 24437Sodium SulfiteHCID 68760612tert-butyl 4-(1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

Product 1

HCID 178452246HCID 178452246, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

I2 (0.920 g, 3.63 mmol) was added to tert-butyl 4-(1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.55 g, 1.81 mmol) and KOH (0.305 g, 5.44 mmol) (crushed by motar and pestle) in DMF (10 mL). The resulting mixture was warmed to 60° C. and stirred for 2 hours. Ether (20 mL) and saturated Na2SO3 (10 mL) were then added. The organic layer was separated, washed with brine and dried over sodium sulfate. After removal of the solvent, the resulting residue was purified by chromatography (hexane:ethyl acetate, 3:1) to give tert-butyl 4-(3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.45 g, 58%) as a solid. MS APCI (+) m/z 430.0 detected. 1H NMR (400 Hz, DMSO-d6) δ 8.31 (d, J=5.2 Hz, 1H), 6.63 (d, J=5.6 Hz, 1H), 3.63 (m, 4H), 3.18 (m, 4H), 1.44 (s, 9H).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the solvent
  5. customthe resulting residue was purified by chromatography (hexane:ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-175da6c8710b4f78853a05e5a7abb433
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08372842B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes