Iodine → HCID 68283346, compound

HRID 1527312Notes

Reaction equation

HRID 1527312 reaction equation
[NH:1]1[C:5]2=[N:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[N:2]1.[I:10]I.[OH-].[K+].Br[CH2:15][C:16]([O:18][CH3:19])=[O:17]>CN(C=O)C.CCOC(C)=O>[I:10][C:3]1[C:4]2[C:5](=[N:6][N:7]=[CH:8][CH:9]=2)[N:1]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[N:2]=1

Participants

7

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 60984Methyl bromoacetateHCID 219482541H-Pyrazolo[3,4-c]pyridazine

Product 1

HCID 68283346HCID 68283346, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1H-pyrazolo[3,4-c]pyridazine [271-75-0] (450 mg, 3.75 mmol) in DMF (10 mL) was added iodine (951 mg, 3.75 mmol) and KOH (525 mg, 9.37 mmol). The mixture was stirred at RT for 16 h until completion of the reaction. Methyl 2-bromoacetate (0.380 mL, 4.12 mmol) was then added to the reaction mixture and stirring was continued at RT for 2 h. The mixture was diluted with EtOAc and washed with water (10 mL), the organic phase was dried (Na2SO4) and evaporated under vacuum. The crude mixture was purified by flash column chromatography on silica gel (c-Hex/EtOAc 66:33) to afford the title compound as a brown solid. TLC, Rf (c-Hex/EtOAc 1:1)=0.40; MS (LC/MS): 318.9 [M+H]+; tR (HPLC conditions c): 3.35 min.

Workup

  1. stirringstirring
  2. waitwas continued at RT for 2 h
  3. washwashed with water (10 mL)
  4. dry with materialthe organic phase was dried (Na2SO4)
  5. customevaporated under vacuum
  6. customThe crude mixture was purified by flash column chromatography on silica gel (c-Hex/EtOAc 66:33)

Sources & evidence

ORD record
ord-204ed26650a94b82bf2faacb26082c88
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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