Water → HCID 90031959, compound

HRID 1048693Notes

Reaction equation

HRID 1048693 reaction equation
[N:1]1[C:2]([CH2:10][OH:11])=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[CH:12]([Si:15](Cl)([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])([CH3:14])[CH3:13].O>ClCCl>[CH:12]([Si:15]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[O:11][CH2:10][C:2]1[N:1]=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[CH:3]=1)([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 139400Triisopropylsilyl chlorideHCID 2795540Imidazo[1,2-a]pyridin-2-ylmethanol

Product 1

HCID 90031959HCID 90031959, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 g (6.55 mmol) of imidazo[1,2-a]pyridin-2-ylmethanol were solubilised in 25 ml of dichloromethane with magnetic stirring and then 2.145 ml (9.82 mmol) of triisopropylsilyl chloride were slowly added. The mixture was stirred at r.t. for 1 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. The crude residue was purified by flash chromatography on a silica gel cartridge (eluent: dichloromethane 100% and then ethyl acetate 100%). 1.85 g (yield=92%) of 2-(((triisopropylsilyl)oxy)methyl)imidazo[1,2-a]pyridine were obtained as a colourless oil. LC-MS: m/z=305 (MH+); UV purity at 254 nm=99%. 1H NMR (300 MHz, DMSO) δ 8.57-8.50 (m, 1H), 7.81 (s, 1H), 7.46 (dd, J=9.1, 0.6 Hz, 1H), 7.19 (ddd, J=9.1, 6.7, 1.3 Hz, 1H), 6.84 (td, J=6.8, 1.1 Hz, 1H), 4.88 (d, J=0.6 Hz, 2H), 1.23-1.11 (m, 3H), 1.11-1.02 (m, 18H).

Workup

  1. stirringThe mixture was stirred at r.t. for 1 h
  2. extractionThe aqueous phase was extracted with 3×50 ml of dichloromethane
  3. washThe combined organic phases were washed with 100 ml of a saturated NaCl aqueous solution
  4. customdried on Na2SO4 which
  5. customwas then removed by filtration
  6. concentrationThe obtained filtrate was concentrated in vacuo
  7. customThe crude residue was purified by flash chromatography on a silica gel cartridge (eluent

Sources & evidence

ORD record
ord-f288da76205e4524b2d9432c294ba541
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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