Water → 2-[3'-(2''-Hydroxyethoxy)phenyl]-6-iodoimidazo[1,2-a]pyridine

HRID 1873375Notes

Reaction equation

HRID 1873375 reaction equation
[O:1]([CH2:19][CH2:20][O:21][C:22]1[CH:23]=[C:24]([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:25]=[CH:26][CH:27]=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:23]=[C:24]([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:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 671359882-[3'-(2''-t-Butyldiphenylsiloxyethoxy)phenyl]-6-iodoimidazo[1,2-a]pyridine

Product 1

HCID 247570172-[3'-(2''-Hydroxyethoxy)phenyl]-6-iodoimidazo[1,2-a]pyridineYield 41%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

477 mg (corresponding to 0.771 mmol) of 2-[3′-(2″-t-butyldiphenylsiloxyethoxy)phenyl]-6-iodoimidazo[1,2-a]pyridine was dissolved in 0.98 mL of tetrahydrofuran, and 0.93 mL of a 1.0 mol/L tetrahydrofuran solution of tetrabutylammoniumfluoride was added thereto. After the reaction mixture was stirred at room temperature for 15 minutes, ammonium chloride solution was added followed by addition of 5.0 mL of water and 2.0 mL of acetonitrile to filter precipitates. The filtered precipitates were washed with water and acetonitrile in this order to obtain 120 mg (corresponding to 0.316 mmol) of 2-[3′-(2″-hydroxyethoxy)phenyl]-6-iodoimidazo[1,2-a]pyridine (FIG. 2-8, Step 5).

Workup

  1. filtrationto filter
  2. customprecipitates
  3. customThe filtered precipitates
  4. washwere washed with water and acetonitrile in this order

Sources & evidence

ORD record
ord-ea0302f50783434abd47c4780601dde9
Source dataset
uspto-grants-2012_11
Patent number
US08303935B2

Reaction notes

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