Water → HCID 42636125, compound

HRID 1873352Notes

Reaction equation

HRID 1873352 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][OH:21])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.O.C(Cl)(Cl)Cl>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][CH2:20][O:21][S:28]([C:25]4[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=4)(=[O:30])=[O:29])=[CH:15][CH:16]=3)[N:10]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 73974-Toluenesulfonyl chlorideHCID 67135683HCID 67135683, compound

Product 1

HCID 42636125HCID 42636125, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

177 mg (corresponding to 0.5 mmol) of 6-bromo-2-[4′-(3″-hydroxypropoxy)phenyl]imidazo[1,2-a]pyridine was dissolved in 10 mL of pyridine, and 197 mg (corresponding to 1.0 mmol) of p-toluenesulfonylchloride was added under an ice bath. After the reaction solution was stirred at room temperature for 16 hours, it was poured into water and extracted three times with chloroform. The combined chloroform layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting crude product was purified by recycle preparative HPLC (HPLC apparatus: LC-908 (under trade name: manufactured by Japan Analytical Industry Co., Ltd.); column: two JAIGEL 2H (under trade name; manufactured by Japan Analytical Industry Co., Ltd.) connected together; mobile phase: chloroform), to obtain 87 mg (corresponding to 0.17 mmol) of 6-bromo-2-[4′-(3″-p-toluenesulfonyloxypropoxy)phenyl]imidazo[1,2-a]pyridine (FIG. 1-2, Step 4).

Workup

  1. extractionextracted three times with chloroform
  2. washThe combined chloroform layer was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting crude product was purified by recycle preparative HPLC (HPLC apparatus

Sources & evidence

ORD record
ord-daa2cd54e3f448b6982a45725b5dab00
Source dataset
uspto-grants-2012_11
Patent number
US08303935B2

Reaction notes

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