Iodine → HCID 178497289, compound

HRID 2403682Notes

Reaction equation

HRID 2403682 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[N:2]1.[OH-].[K+].[I:16]I.S(=O)(=O)(O)[O-].[Na+]>CN(C)C=O>[I:16][C:3]1[C:4]2[C:9](=[CH:8][C:7]([C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=2)[NH:1][N:2]=1

Participants

6

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 286535methyl 1H-indazole-6-carboxylateHCID 516919Sodium Bisulfate

Product 1

HCID 178497289HCID 178497289, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 1H-indazole-6-carboxylate (865 mg, 4.91 mmol) in N,N-dimethylformamide (12 mL) was added potassium hydroxide (840 mg, 3.05 mmol) followed by iodine (1.54 g, 5.9 mmol). The mixture was stirred at room temperature for 3 hours. Sodium bisulfate (30 mL of 5% aqueous) was added and the mixture was extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified via flash column chromatography (5-65% ethyl acetate/heptanes) to afford methyl 3-iodo-1H-indazole-6-carboxylate as a colorless solid (1.16 g, 78%). 1H NMR (400 MHz, DMSO-d6, δ): 13.84 (s, 1 H), 8.13 (s, 1 H), 7.72 (d, J=8.4 Hz, 1 H), 7.54 (d, J=8.6 Hz, 1 H), 3.87 (s, 3 H).

Workup

  1. extractionthe mixture was extracted with ethyl acetate twice
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified via flash column chromatography (5-65% ethyl acetate/heptanes)

Sources & evidence

ORD record
ord-43c28592d40e46de85812fcd7ab80977
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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