Ammonium Chloride → HCID 68719801, compound

HRID 1948883Notes

Reaction equation

HRID 1948883 reaction equation
[Br:1][C:2]1[C:3]([CH3:28])=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][O:20][Si](C(C)(C)C)(C)C)=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>O1CCCC1>[Br:1][C:2]1[C:3]([CH3:28])=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][OH:20])=[CH:15][CH:16]=3)[N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 68717541HCID 68717541, compound

Product 1

HCID 68719801HCID 68719801, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

571 mg (corresponding to 1.24 mmol) of 6-bromo-2-[4′-(2″-t-butyldimethylsiloxyethoxy)phenyl]-7-methylimidazo[1,2-a]pyridine was dissolved in 3.0 mL of tetrahydrofuran, and 1.24 mL of a 1.0 mol/L solution in tetrahydrofuran of tetrabutylammoniumfluoride was added thereto. After the reaction mixture was stirred at room temperature for 20 minutes, an aqueous ammonium chloride solution was added, and extracted three times with ethyl acetate. The combined ethyl acetate layers were dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting crude product was washed with water and ethyl acetate, to obtain 320 mg (corresponding to 0.922 mmol) of 6-bromo-2-[4′-(2″-hydroxyethoxy)phenyl]-7-methylimidazo[1,2-a]pyridine (FIG. 9, Step 5).

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined ethyl acetate layers were dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washThe resulting crude product was washed with water and ethyl acetate

Sources & evidence

ORD record
ord-26a8a9c7315248d0a12ca3b7a1b07fa5
Source dataset
uspto-grants-2013_03
Patent number
US08399672B2

Reaction notes

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