Iodine → HCID 66920616, compound

HRID 1880408Notes

Reaction equation

HRID 1880408 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([C:12]([O:14]C)=[O:13])[CH:6]=[C:7]2C=1N[N:9]=[CH:8]2)[CH3:2].C([O-])([O-])=O.[K+].[K+].[I:22]I.OS([O-])=O.[Na+].C[N:30]([CH:32]=O)[CH3:31]>CCOC(C)=O.C1COCC1>[CH3:31][N:30]1[C:32]2[C:7](=[CH:6][C:5]([C:12]([OH:14])=[O:13])=[CH:4][C:3]=2[CH2:1][CH3:2])[C:8]([I:22])=[N:9]1

Participants

7

Reactant 5

HCID 807IodineHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 23665763Sodium BisulfiteHCID 60144278methyl 7-ethyl-1H-indazole-5-carboxylate

Product 1

HCID 66920616HCID 66920616, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

To a solution of methyl 7-ethyl-1H-indazole-5-carboxylate (252 mg, 1.23 mmol) in DMF (10 mL) was added K2CO3 (550 mg, 3.98 mmol) and I2 (370 mg, 1.46 mmol). The mixture was stirred at room temperature overnight. To this was then added 5% NaHSO3 (10 mL) followed by 1:1 EtOAc/THF (50 mL). The organic layer was isolated, dried over Na2SO4, filtered and concentrated. The solid was suspended in CH2Cl2, collected by filtration and dried to provide methyl 7-ethyl-3-iodo-1H-indazole-5-carboxylic acid (298 mg, 73%).

Workup

  1. customThe organic layer was isolated
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. filtrationcollected by filtration
  6. customdried

Sources & evidence

ORD record
ord-627a4225c37342aba262337dc9afa345
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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