Water → HCID 90031755, compound

HRID 1048694Notes

Reaction equation

HRID 1048694 reaction equation
[CH:1]([Si:4]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[O:5][CH2:6][C:7]1[N:8]=[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]2[CH:15]=1)([CH3:3])[CH3:2].[I:22]N1C(=O)CCC1=O.O>C(#N)C>[I:22][C:15]1[N:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]2=[N:8][C:7]=1[CH2:6][O:5][Si:4]([CH:1]([CH3:3])[CH3:2])([CH:16]([CH3:18])[CH3:17])[CH:19]([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 90031959HCID 90031959, compound

Product 1

HCID 90031755HCID 90031755, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.85 g (6.08 mmol) of 2-(((triisopropylsilyl)oxy)methyl)imidazo[1,2-a]pyridine were solubilised in 25 ml of acetonitrile with magnetic stirring, to this solution were added 1.409 g (6.08 mmol) of N-iodosuccinimide. The mixture was stirred at r.t. for 16 h before being treated with 100 ml of water. The aqueous phase was extracted with 3×50 ml of dichloromethane. The combined organic phases were washed with 100 ml of a saturated NaCl aqueous solution, dried on Na2SO4 which was then removed by filtration. The obtained filtrate was concentrated in vacuo. 2.29 g (yield=83%) of 3-iodo-2-(((triisopropylsilyl)oxy)methyl)imidazo[1,2-a]pyridine were obtained as a pale yellow solid. LC-MS: m/z=431 (MH+); UV purity at 254 nm=95%.

Workup

  1. extractionThe aqueous phase was extracted with 3×50 ml of dichloromethane
  2. washThe combined organic phases were washed with 100 ml of a saturated NaCl aqueous solution
  3. customdried on Na2SO4 which
  4. customwas then removed by filtration
  5. concentrationThe obtained filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-245a9104a46f48a7a4d832c0542c5572
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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