Water → HCID 68718916, compound

HRID 1948879Notes

Reaction equation

HRID 1948879 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)=[C:24]([O:38][CH3:39])[CH:23]=1)[Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])O.[Na+].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)=[C:24]([O:38][CH3:39])[CH:23]=1

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 68719210HCID 68719210, compound

Product 1

HCID 68718916HCID 68718916, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

200 mg (corresponding to 0.274 mmol) of 2-[4′-(2″-t-butyldiphenylsiloxyethoxy)-2′-methoxyphenyl]-6-iodoimidazo[1,2-a]pyridine was dissolved in 2.0 mL of tetrahydrofuran, and 0.33 mL of a 1.0 mol/L tetrahydrofuran solution of tetrabutylammoniumfluoride was added thereto. After the reaction mixture was stirred at room temperature for 4 hours, an aqueous sodium hydrogencarbonate solution was added followed by addition of 5.0 mL of water and 1.0 mL of acetonitrile to filter precipitates. The filtered precipitates were washed with water and acetonitrile in this order to obtain 103 mg (corresponding to 0.251 mmol) of 2-[4′-(2″-hydroxyethoxy)-2′-methoxyphenyl]-6-iodoimidazo[1,2-a]pyridine (FIG. 7, Step 6).

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-d2d6fe170c9c478eba08d6700f85cc0e
Source dataset
uspto-grants-2013_03
Patent number
US08399672B2

Reaction notes

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