Water → 2-[4'-(3''-Hydroxypropoxy)phenyl]-6-iodoimidazo[1,2-a]pyridine

HRID 1890202Notes

Reaction equation

HRID 1890202 reaction equation
[O:1]([CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:20]=[C:21]3[CH:26]=[CH:25][C:24]([I:27])=[CH:23][N:22]3[CH:28]=2)=[CH:15][CH:14]=1)[Si](C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+].O>O1CCCC1.C(#N)C>[OH:1][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[N:20]=[C:21]3[CH:26]=[CH:25][C:24]([I:27])=[CH:23][N:22]3[CH:28]=2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 671360922-[4'-(3''-t-Butyldimethylsiloxypropoxy)phenyl]-6-iodoimidazo[1,2-a]pyridine

Product 1

HCID 247571022-[4'-(3''-Hydroxypropoxy)phenyl]-6-iodoimidazo[1,2-a]pyridineYield 87.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1.52 g (corresponding to 2.99 mmol) of 2-[4′-(3″-t-butyldimethylsiloxypropoxy)phenyl]-6-iodoimidazo[1,2-a]pyridine was dissolved in 5.0 mL of tetrahydrofuran, and 2.99 mL of a 1.0 mol/L tetrahydrofuran solution of tetrabutylammoniumfluoride was added thereto. After the reaction mixture was stirred at room temperature for 30 minutes, ammonium chloride solution was added followed by the addition of 10 mL of water and 5.0 mL of acetonitrile to filter precipitates. The filtered precipitates were washed with water and acetonitrile in this order, to obtain 1.03 g (corresponding to 2.61 mmol) of 2-[4′-(3″-hydroxypropoxy)phenyl]-6-iodoimidazo[1,2-a]pyridine (FIG. 2-10, 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-aff00e9753ba4e44b2f816bee3fc7864
Source dataset
uspto-grants-2013_08
Patent number
US08506930B2

Reaction notes

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