Water → 2-(4-(6-Iodoimidazo(1,2-a)pyridin-2-yl)phenoxy)ethanol

HRID 1890193Notes

Reaction equation

HRID 1890193 reaction equation
[O:1]([CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[N:29]=[C:30]3[CH:35]=[CH:34][C:33]([I:36])=[CH:32][N:31]3[CH:37]=2)=[CH:24][CH:23]=1)[Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+].O>O1CCCC1.C(#N)C>[OH:1][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[N:29]=[C:30]3[CH:35]=[CH:34][C:33]([I:36])=[CH:32][N:31]3[CH:37]=2)=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 671360362-[4'-(2''-t-Butyldiphenylsiloxyethoxy)phenyl]-6-iodoimidazo[1,2-a]pyridine

Product 1

HCID 247570132-(4-(6-Iodoimidazo(1,2-a)pyridin-2-yl)phenoxy)ethanolYield 100%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

368 mg (corresponding to 0.595 mmol) of 2-[4′-(2″-t-butyldiphenylsiloxyethoxy)phenyl]-6-iodoimidazo[1,2-a]pyridine was dissolved in 1.0 mL of tetrahydrofuran (THF), and 0.70 mL of a 1.0 mol/L tetrahydrofuran solution of tetrabutylammoniumfluoride (TBAF) was added thereto. After the reaction mixture was stirred at room temperature for 2 hours, ammonium chloride solution was added, followed by addition of 5.0 mL of water and 2.0 mL of acetonitrile. Then, precipitates were filtered. The filtered precipitates were washed with water and acetonitrile in this order, to obtain 226 mg (corresponding to 0.595 mmol) of 2-[4′-(2″-hydroxyethoxy)phenyl]-6-iodoimidazo[1,2-a]pyridine (FIG. 2-1, Step 5).

Workup

  1. customThen, precipitates
  2. filtrationwere filtered
  3. customThe filtered precipitates
  4. washwere washed with water and acetonitrile in this order

Sources & evidence

ORD record
ord-4f47449deaca450bb731272c27b53374
Source dataset
uspto-grants-2013_08
Patent number
US08506930B2

Reaction notes

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