Potassium Carbonate → HCID 67261255, compound

HRID 79371

Reaction equation

HRID 79371 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:8]=[C:7]([CH3:9])[N:6]([CH3:10])[N:5]=1.[I:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][C:19]=2[N+:21]([O-:23])=[O:22])[NH:14][N:13]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:10][N:6]1[C:7]([CH3:9])=[CH:8][C:4]([CH2:3][N:14]2[C:15]3[C:20](=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][CH:16]=3)[C:12]([I:11])=[N:13]2)=[N:5]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 669375573-(chloromethyl)-1,5-dimethyl-1H-pyrazole hydrochlorideHCID 178526562HCID 178526562, compound

Product 1

HCID 67261255HCID 67261255, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-(chloromethyl)-1,5-dimethyl-1H-pyrazole hydrochloride (5.01 g, 27.7 mmol) in DMF (50 mL) was added 3-iodo-4-nitro-1H-indazole (8.00 g, 27.7 mmol) and K2CO3 (15.3 g, 111 mmol). The reaction mixture was stirred for 20 hours. The mixture was concentrated under reduced pressure to remove most of the DMF. The residue was diluted with DCM (100 mL) and washed with H2O. The organic phase was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by silica gel chromatography (EtOAc/Hexane 1:3) to provide the product (8.35 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto remove most of the DMF
  3. additionThe residue was diluted with DCM (100 mL)
  4. washwashed with H2O
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (EtOAc/Hexane 1:3)

Sources & evidence

ORD record
ord-ba84414bbc5a4f3185805b3965961618
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Linked notes

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