Iodine → HCID 178519327, compound

HRID 2383564Notes

Reaction equation

HRID 2383564 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]=[O:11])[CH:8]=2)[CH:3]=[N:2]1.C([O-])([O-])=O.[K+].[K+].[I:18]I.[O-]S(S([O-])=O)=O.[Na+].[Na+]>CN(C=O)C.O>[I:18][C:3]1[C:4]2[C:9](=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][CH:5]=2)[NH:1][N:2]=1

Participants

7

Reactant 4

HCID 807IodineHCID 11430Potassium Carbonate2×HCID 24489Sodium DithioniteHCID 185383681H-Indazole-6-carbaldehyde

Product 1

HCID 178519327HCID 178519327, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1H-indazole-6-carbaldehyde (2.00 g, 13.7 mmol), K2CO3 (3.79 g, 27.4 mmol) in DMF (15 mL) was added dropwise a solution of I2 (5.91 g, 23.3 mmol) in DMF (15 mL) and the reaction allowed to stir for two h. An aqueous solution consisting of Na2S2O4 (3.30 g)/K2CO3 (0.20 g)/H2O (30 mL) was then added and the solution stirred for one h. The product was then precipitated by pouring the solution over ice-water (300 mL) and collected by vacuum filtration to give after drying 3.02 g, 81% of a beige powder. 1H NMR (400 MHz, CD3OD) δ 10.11 (s, 1H), 8.11 (s, 1H), 7.74 (d, J=8.34 Hz, 1H), 7.62 (d, J=8.34 Hz, 1H); MS ESI 272.9 [M+H]+, calcd for [C8H5IN2O+H]+ 272.95.

Workup

  1. additionwas then added
  2. stirringthe solution stirred for one h
  3. customThe product was then precipitated
  4. additionby pouring the solution over ice-water (300 mL)
  5. filtrationcollected by vacuum filtration
  6. customto give
  7. dry with materialafter drying 3.02 g, 81% of a beige powder

Sources & evidence

ORD record
ord-05dcac53af2944f78828ab58df786910
Source dataset
uspto-grants-2012_09
Patent number
US08263596B2

Reaction notes

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