Iodine → HCID 178506566, compound

HRID 245784

Reaction equation

HRID 245784 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[I:10]I.[OH-].[K+]>CN(C=O)C>[I:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][N:2]=1

Participants

5

Reactant 3

HCID 807IodineHCID 92211H-IndazoleHCID 14797Potassium Hydroxide

Product 1

HCID 178506566HCID 178506566, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 50 mL round-bottomed flask, indazole (0.80 g, 6.8 mmol) was dissolved in DMF (14 mL). Iodine (3.4 g, 13.5 mmol) was added followed by potassium hydroxide (1.47 g, 26.2 mmol). The dark reaction mixture was stirred at room temperature for 1.25 h then was quenched with 10% aq NaHSO3 and extracted with diethyl ether (2×). The combined organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated to give 1.65 g (95%) of 3-iodo-1H-indazole as a light yellow solid. 1H NMR (CDCl3, 300 MHz): δ (ppm) 10.56 (br. s, 1H), 7.47-7.57 (m, 3H), 7.23-7.30 (m, 1H).

Workup

  1. customThe dark reaction mixture
  2. customthen was quenched with 10% aq NaHSO3
  3. extractionextracted with diethyl ether (2×)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialthen dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-95d34199a9a34642b649aa1b6be2f693
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Linked notes

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