Water → HCID 68718917, compound

HRID 1948875Notes

Reaction equation

HRID 1948875 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][C:3]=1[I:19].C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][CH2:28][CH2:29][F:30].O>CN(C)C=O.C(Cl)(Cl)Cl>[F:30][CH2:29][CH2:28][CH2:27][O: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][C:3]=1[I:19]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67699Propane, 1-bromo-3-fluoro-HCID 68719554HCID 68719554, compound

Product 1

HCID 68718917HCID 68718917, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

279 mg (corresponding to 0.763 mmol) of 2-(4′-hydroxy-3′-iodophenyl)-6-methoxyimidazo[1,2-a]pyridine that was dissolved in 10 mL of N,N-dimethylformamide, and 317 mg (corresponding to 2.29 mmol) of potassium carbonate was added thereto. The mixture was supplemented with 105 μL (corresponding to 1.15 mmol) of 1-bromo-3-fluoropropane, and then the solution was stirred at room temperature for 21 hours. After the completion of the reaction, the reaction solution was poured into water, and extracted three times with chloroform. The combined chloroform layers were 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 262 mg (corresponding to 0.614 mmol) of 2-[4′-(3″-fluoropropoxy)-3′-iodophenyl]-6-methoxyimidazo[1,2-a]pyridine (FIG. 1, Step 7).

Workup

  1. customAfter the completion of the reaction
  2. extractionextracted three times with chloroform
  3. washThe combined chloroform layers were washed with a saturated sodium chloride solution
  4. dry with materialdried 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-4b6d3673d6434273a3ac4b60e154798f
Source dataset
uspto-grants-2013_03
Patent number
US08399672B2

Reaction notes

Loading…