N-Iodosuccinimide → HCID 178506575, compound

HRID 2203348Notes

Reaction equation

HRID 2203348 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[N:2]1.[I:10]N1C(=O)CCC1=O>C(#N)C.O>[I:10][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:1][N:2]=1

Participants

5

Reactant 2

HCID 120273N-Iodosuccinimide2×HCID 27558501H-pyrazolo(3,4-b)pyridine

Product 1

HCID 178506575HCID 178506575, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

A solution of the intermediate from Step A above (14.3 g, 120 mmol) and N-iodosuccinimide (28.4 g, 126 mmol) in acetonitrile (210 mL) was heated at 75° C. After 17 hours, N-iodosuccinimide (5.4 g, 24 mmol) was added and the reaction solution stirred at 75° C. for an additional 1.5 hours. The reaction solution was cooled to room temperature and diluted with water. The slurry was concentrated in vacuo to remove most of the acetonitrile. The solid was collected, washed with water, and dried under a vacuum with a nitrogen sweep for 17 hours to give the title compound. 1H NMR (400 MHz, CH3CN-d3): δ 11.85 (s, 1H); 8.55 (dd, J=4.53, 1.53 Hz, 1H); 7.87 (dd, J=8.11, 1.53 Hz, 1H); 7.24 (dd, J=8.11, 4.51 Hz, 1H). m/z=246.1 (M+H).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. concentrationThe slurry was concentrated in vacuo
  3. customto remove most of the acetonitrile
  4. customThe solid was collected
  5. washwashed with water
  6. customdried under a vacuum with a nitrogen sweep for 17 hours

Sources & evidence

ORD record
ord-b47d22361a69430b85dc9c2aa8f9cc08
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

Loading…