Water → 2-[4'-(3''-Fluoropropoxy)phenyl]-6-methoxyimidazo[1,2-a]pyridine

HRID 2059505Notes

Reaction equation

HRID 2059505 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]([O:16][CH3:17])=[CH:12][N:11]3[CH:18]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][CH2:27][CH2:28][F:29].O>C(Cl)(Cl)Cl>[F:29][CH2:28][CH2:27][CH2:26][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]([O:16][CH3:17])=[CH:12][N:11]3[CH:18]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67699Propane, 1-bromo-3-fluoro-HCID 3982884-(6-Methoxyimidazo[1,2-a]pyridin-2-yl)phenol

Product 1

HCID 248217932-[4'-(3''-Fluoropropoxy)phenyl]-6-methoxyimidazo[1,2-a]pyridineYield 63%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

242 mg (corresponding to 1.0 mmol) of 2-(4′-hydroxyphenyl)-6-methoxyimidazo[1,2-a]pyridine that was sufficiently dried to remove moisture was dissolved in 10 L of N,N-dimethylformamide, and 418 mg (corresponding to 3.0 mmol) of potassium carbonate was added thereto. The mixture was supplemented with 140 μL (corresponding to 1.5 mmol) of 1-bromo-3-fluoropropane, and then was stirred at room temperature for 18 hours. After the completion of the reaction, the reaction solution was poured into water and extracted three times with chloroform. The combined chloroform layer was washed once with water and once 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 189 mg (corresponding to 0.63 mmol) of 2-[4′-(3″-fluoropropoxy)phenyl]-6-methoxyimidazo[1,2-a]pyridine (hereinafter referred to as Compound 1) (FIG. 2, Step 6).

Workup

  1. customto remove moisture
  2. dissolutionwas dissolved in 10 L of N,N-dimethylformamide
  3. customAfter the completion of the reaction
  4. extractionextracted three times with chloroform
  5. washThe combined chloroform layer was washed once with water and once with a saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting crude product was purified by recycle preparative HPLC (HPLC apparatus

Sources & evidence

ORD record
ord-9479d13a8d1746ebbe026f8062d709fe
Source dataset
uspto-grants-2012_10
Patent number
US08277777B2

Reaction notes

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