Sodium Chloride → HCID 68717541, compound

HRID 1948882Notes

Reaction equation

HRID 1948882 reaction equation
[Br:1][C:2]1[C:3]([CH3:18])=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30].[Cl-].[Na+]>CN(C)C=O>[Br:1][C:2]1[C:3]([CH3:18])=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:26][CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 68717459HCID 68717459, compound

Product 1

HCID 68717541HCID 68717541, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

462 mg (corresponding to 1.52 mmol) of 6-bromo-2-(4′-hydroxyphenyl)-7-methylimidazo[1,2-a]pyridine was dissolved in 10 mL of dimethylformamide, and 630 mg (corresponding to 4.56 mmol) of potassium carbonate was added thereto. Then, 400 mg (corresponding to 1.67 mmol) of 1-bromo-2-(t-butyldimethylsiloxy)ethane was added thereto. After the reaction mixture was stirred at room temperature for 4 days, a saturated aqueous sodium 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 purified by silica gel column chromatography (ethyl acetate) to obtain 571 mg (corresponding to 1.24 mmol) of 6-bromo-2-[4′-(2″-t-butyldimethylsiloxyethoxy)phenyl]-7-methylimidazo[1,2-a]pyridine (FIG. 9, Step 4).

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. customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-9a662c1df3fb46a79aa7efc53fc4ab32
Source dataset
uspto-grants-2013_03
Patent number
US08399672B2

Reaction notes

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