3-Methoxybenzoic Acid → HCID 23025927, compound

HRID 1437488Notes

Reaction equation

HRID 1437488 reaction equation
[O:1]([C:8]1[N:13]=[C:12]([NH2:14])[C:11]([NH2:15])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21](O)=O.[OH-].[Na+]>P(Cl)(Cl)(Cl)=O>[O:1]([C:8]1[N:13]=[C:12]2[N:14]=[C:21]([C:20]3[CH:24]=[CH:25][CH:26]=[C:18]([O:17][CH3:16])[CH:19]=3)[NH:15][C:11]2=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 114613-Methoxybenzoic AcidHCID 14798Sodium HydroxideHCID 23025814HCID 23025814, compound

Product 1

HCID 23025927HCID 23025927, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
140 °C

Procedure

6-Phenoxy-2,3-pyridine diamine (Compound of Reference Example 115) (0.2 g) and 3-methoxybenzoic acid (0.08 g) were dissolved in phosphorus oxychloride (5 ml) and the solution was stirred at 140° C. for 4 hours. The reaction mixture was poured onto ice, neutralized with 8 N sodium hydroxide solution and extracted with ethyl acetate-tetrahydrofuran (3:1, v/v). The organic layer was washed with water and dried over MgSO4. The solvent was distilled off under reduced pressure, and the resulting crystals were collected by filtration to obtain 5-phenoxy-2-(3-methoxyphenyl)-1H-imidazo[4,5-b]pyridine (0.04 g, 23%).

Workup

  1. additionThe reaction mixture was poured onto ice
  2. extractionextracted with ethyl acetate-tetrahydrofuran (3:1
  3. washThe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. distillationThe solvent was distilled off under reduced pressure
  6. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-b779d654e4fa494db5296928e63463ee
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

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