N-Iodosuccinimide → HCID 178477877, compound

HRID 2203333Notes

Reaction equation

HRID 2203333 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][CH:3]=1.C1C(=O)N([I:18])C(=O)C1>C(#N)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([I:18])=[N:7][NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 4175246-chloro-1H-indazole

Product 1

HCID 178477877HCID 178477877, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

An acetonitrile solution (250 mL) containing the intermediate from Step A (6.14 g, 40.2 mmol) and NIS (9.33 g, 41.4 mmol) was heated at 60° C. for 3 hours. The reaction solution was cooled to room temperature and concentrated to approximately 70 mL volume. The reaction was then diluted with water (ca 400 mL). The suspension was stirred for 10 minutes and then filtered. The solid was air dried on the filter to give the indicated product. The material was used in Step C without further purification. 1H NMR (400 MHz, CH 3 CN-d3): δ 1.52 (broad s, 1H); 7.62 (d, J=1.7 Hz, 1H); 7.44 (d, J=8.6 Hz, 1H); 7.21 (dd, J=8.6, 1.7 Hz, 1H). m/z=279.0 (M+H).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. concentrationconcentrated to approximately 70 mL volume
  3. additionThe reaction was then diluted with water (ca 400 mL)
  4. filtrationfiltered
  5. customdried on the
  6. filtrationfilter
  7. customto give the indicated product
  8. customThe material was used in Step C without further purification

Sources & evidence

ORD record
ord-669def609c0548d19749e733dd84179b
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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