Sodium Chloride → 2-[4'-(3''-t-Butyldimethylsiloxypropoxy)phenyl]-6-iodoimidazo[1,2-a]pyridine

HRID 222228Notes

Reaction equation

HRID 222228 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([I:16])=[CH:12][N:11]3[CH:17]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][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>[O:28]([CH2:27][CH2:26][CH2:25][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([I:16])=[CH:12][N:11]3[CH:17]=2)=[CH:6][CH:7]=1)[Si:29]([C:32]([CH3:34])([CH3:33])[CH3:35])([CH3:30])[CH3:31]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 247570112-(4'-Hydroxyphenyl)-6-iodoimidazo[1,2-a]pyridine

Product 1

HCID 671360922-[4'-(3''-t-Butyldimethylsiloxypropoxy)phenyl]-6-iodoimidazo[1,2-a]pyridineYield 50.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.00 g (corresponding to 5.95 mmol) of 2-(4′-hydroxyphenyl)-6-iodoimidazo[1,2-a]pyridine was dissolved in 30.0 mL of dimethylformamide, and 2.47 g (corresponding to 17.9 mmol) of potassium carbonate was added. Then, 1.51 g (corresponding to 5.95 mmol) of 1-bromo-3-(t-butyldimethylsiloxy)propane was added thereto. After the reaction mixture was stirred at room temperature for 8 days, it was supplemented with a saturated sodium chloride aqueous solution, 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 (elution solvent: hexane/ethyl acetate=1/1) to obtain 1.52 g (corresponding to 2.99 mmol) of 2-[4′-(3″-t-butyldimethylsiloxypropoxy)phenyl]-6-iodoimidazo[1,2-a]pyridine (FIG. 10, 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 (elution solvent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-50563f2a3b7544e59415dcb52472f83b
Source dataset
uspto-grants-2012_06
Patent number
US08207189B2

Reaction notes

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