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

HRID 222224Notes

Reaction equation

HRID 222224 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][O:27][Si:28]([C:41]([CH3:44])([CH3:43])[CH3:42])([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[Cl-].[Na+]>CN(C)C=O>[O:27]([CH2:26][CH2:25][O:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1)[Si:28]([C:41]([CH3:43])([CH3:42])[CH3:44])([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 10915442(2-Bromoethoxy)(tert-butyl)diphenylsilaneHCID 671362372-(3'-Hydroxyphenyl)-6-iodoimidazo[1,2-a]pyridine

Product 1

HCID 671359882-[3'-(2''-t-Butyldiphenylsiloxyethoxy)phenyl]-6-iodoimidazo[1,2-a]pyridineYield 86.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

300 mg (corresponding to 0.893 mmol) of 2-(3′-hydroxyphenyl)-6-iodoimidazo[1,2-a]pyridine was dissolved in 5.0 mL of dimethylformamide, and 370 mg (corresponding to 2.68 mmol) of potassium carbonate was added thereto. Then, 357 mg (corresponding to 0.982 mmol) of 1-bromo-2-(t-butyldiphenylsiloxy)ethane was added thereto. After the reaction mixture was stirred at 90° C. for 2 hours, a saturated sodium chloride aqueous 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 (elution solvent: hexane/ethyl acetate=3/1) to obtain 477 mg (corresponding to 0.771 mmol) of 2-[3′-(2″-t-butyldiphenylsiloxyethoxy)phenyl]-6-iodoimidazo[1,2-a]pyridine (FIG. 8, 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=3/1)

Sources & evidence

ORD record
ord-87face66b410404ebb15ad8e1d86faa7
Source dataset
uspto-grants-2012_06
Patent number
US08207189B2

Reaction notes

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