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

HRID 222228ノート

反応式

HRID 222228 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-50563f2a3b7544e59415dcb52472f83b
出典データセット
uspto-grants-2012_06
特許番号
US08207189B2

反応ノート

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