Water → HCID 24756926, compound

HRID 2059519Notes

Reaction equation

HRID 2059519 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]([OH:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][CH2:27][F:28].O>C(Cl)(Cl)Cl>[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][CH2:25][CH2:26][CH2:27][F:28])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67699Propane, 1-bromo-3-fluoro-HCID 24864014HCID 24864014, compound

Product 1

HCID 24756926HCID 24756926, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

290 mg (corresponding to 1.0 mmol) of 6-bromo-2-(4′-hydroxyphenyl)imidazo[1,2-a]pyridine that was sufficiently dried to remove moisture was dissolved in 10 mL of N,N-dimethylformamide, and 413 mg (corresponding to 3.0 mmol) of potassium carbonate was added thereto. 138 μL (corresponding to 1.5 mmol) of 1-bromo-3-fluoropropane was added to the resulting solution, and then the solution was stirred at room temperature for 20.5 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 with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and 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 302 mg (corresponding to 0.866 mmol) of 6-bromo-2-[4′-(3″-fluoropropoxy)phenyl]imidazo[1,2-a]pyridine (FIG. 7, Step 3).

Workup

  1. customto remove moisture
  2. dissolutionwas dissolved in 10 mL of N,N-dimethylformamide
  3. customAfter the completion of the reaction
  4. extractionextracted three times with chloroform
  5. washThe combined chloroform layer was washed 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-92a1a0f137be4dba8cd1eb37c78c9bb3
Source dataset
uspto-grants-2012_10
Patent number
US08277777B2

Reaction notes

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