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

HRID 222219노트

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HRID 222219 반응식
[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][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]=[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: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

참가 물질

6

반응물 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 10915442(2-Bromoethoxy)(tert-butyl)diphenylsilaneHCID 247570112-(4'-Hydroxyphenyl)-6-iodoimidazo[1,2-a]pyridine

생성물 1

HCID 671360362-[4'-(2''-t-Butyldiphenylsiloxyethoxy)phenyl]-6-iodoimidazo[1,2-a]pyridine수율 100%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

200 mg (corresponding to 0.595 mmol) of 2-(4′-hydroxyphenyl)-6-iodoimidazo[1,2-a]pyridine was dissolved in 3.0 mL of dimethylformamide, and 247 mg (corresponding to 1.79 mmol) of potassium carbonate was added thereto. Then, 259 mg (corresponding to 0.714 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=2/1) to obtain 368 mg (corresponding to 0.595 mmol) of 2-[4′-(2″-t-butyldiphenylsiloxyethoxy)phenyl]-6-iodoimidazo[1,2-a]pyridine (FIG. 1, Step 4).

후처리

  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=2/1)

출처 및 근거

ORD 기록
ord-8308e3c610aa4b649b23972f66d7e04c
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207189B2

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