Water → HCID 24821795, compound

HRID 2059514Notes

Reaction equation

HRID 2059514 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][CH:13]=[CH:12][N:11]3[CH:16]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][CH2:25][CH2:26][F:27].O>CN(C)C=O.C(Cl)(Cl)Cl>[F:27][CH2:26][CH2:25][CH2:24][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]3[CH:16]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67699Propane, 1-bromo-3-fluoro-HCID 818333Phenol, 4-imidazo[1,2-a]pyridin-2-yl-

Product 1

HCID 24821795HCID 24821795, compoundYield 51.9%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

398 mg (corresponding to 1.89 mmol) of 2-(4′-hydroxyphenyl)imidazo[1,2-a]pyridine was dissolved in 15 mL of N,N-dimethylformamide, and 788 mg (corresponding to 5.7 mmol) of potassium carbonate was added thereto. 260 μL (corresponding to 2.8 mmol) of 1-bromo-3-fluoropropane was added to the resulting mixture, and the mixture was stirred for 20.5 hours at room temperature. 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 with water and a saturated sodium chloride solution, and then 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 of JAIGEL 2H (under trade name; manufactured by Japan Analytical Industry Co., Ltd.) connected together; mobile phase: chloroform), to obtain 264 mg (corresponding to 0.98 mmol) of 2-[4′-(3″-fluoropropoxy)phenyl]imidazo[1,2-a]pyridine (hereinafter referred to as Compound 3) (FIG. 4, Step 3).

Workup

  1. customAfter the completion of the reaction
  2. extractionextracted three times with chloroform
  3. washThe combined chloroform layer was washed with water
  4. dry with materiala saturated sodium chloride solution, and then dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting crude product was purified by recycle preparative HPLC (HPLC apparatus

Sources & evidence

ORD record
ord-5ed3b8b9df2f47f8be13ee64e73f70ac
Source dataset
uspto-grants-2012_10
Patent number
US08277777B2

Reaction notes

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