3-Chlorobenzoic Acid → HCID 23025516, compound

HRID 1437458Notes

Reaction equation

HRID 1437458 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14](O)=O.[OH-].[Na+]>>[Br:9][C:5]1[CH:6]=[C:7]2[NH:8][C:14]([C:13]3[CH:17]=[CH:18][CH:19]=[C:11]([Cl:10])[CH:12]=3)=[N:1][C:2]2=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 4473-Chlorobenzoic AcidHCID 14798Sodium HydroxideHCID 6911565-Bromopyridine-2,3-diamine

Product 1

HCID 23025516HCID 23025516, compoundYield 69.2%

Conditions

Temperature
170 °C

Procedure

A mixture of 2,3-diamino-5-bromopyridine (Compound of Reference Example 1) (1.32 g), 3-chlorobenzoic acid (1.10 g) and polyphosphoric acid (30 g) was stirred at 170° C. for 2 hours. The mixture was poured onto ice, neutralized with 8N-sodium hydroxide and extracted with ethyl acetate-tetrahydrofuran (3:1, v/v). The organic layer was washed with water and dried with MgSO4. The solvent was distilled off under reduced pressure, and resulting crystals were collected by filtration to obtain 6-bromo-2-(3-chlorophenyl)-1H-imidazo[4,5-b]pyridine (1.50 g, 69%).

Workup

  1. additionThe 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 with MgSO4
  5. distillationThe solvent was distilled off under reduced pressure
  6. customresulting crystals
  7. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-0ad29c1f8f6641a1af93cde38cbe6dc8
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

Loading…