Triethylamine → 3-(4-Bromo-2-chlorophenyl)-4-chloro-1H-diimidazo[1,2-a:4',5'-d]pyridin-2(3H)-one

HRID 558213Notes

Reaction equation

HRID 558213 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14](C(O)=O)=[CH:13][N:12]3[CH:18]=[CH:19][N:20]=[C:11]3[C:10]=2[Cl:21])=[C:4]([Cl:22])[CH:3]=1.CC[N:25]([CH2:28]C)CC.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:37])=CC=1>CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]3=[C:10]([Cl:21])[C:11]4[N:12]([CH:18]=[CH:19][N:20]=4)[CH:13]=[C:14]3[NH:25][C:28]2=[O:37])=[C:4]([Cl:22])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 115964897-(4-Bromo-2-chlorophenylamino)-8-chloroimidazo[1,2-a]pyridine-6-carboxylic acid

Product 1

HCID 595194533-(4-Bromo-2-chlorophenyl)-4-chloro-1H-diimidazo[1,2-a:4',5'-d]pyridin-2(3H)-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 7-(4-bromo-2-chlorophenylamino)-8-chloroimidazo[1,2-a]pyridine-6-carboxylic acid (152 mg, 0.35 mmol) (HCl salt) in 5 ml EtOAc was added NEt3 (0.14 ml, 102 mg, 1 mmol) and the mixture was stirred for 5 min upon the suspension turned into a solution. The solvents were removed in vacuo and the residue was dried in oil-pump vacuo. This residue was suspended in 4.5 ml anhydrous toluene and it was ultrasonicated for 1 min. DPPA (0.1 ml, 124 mg, 0.44 mmol) was added and the suspension was heated with stirring under argon at 125° C. oil bath temperature to reflux for 5 h. The initial suspension turns into a dark solution after about 30 min. heating, and then a precipitate is formed after about another 30 min. reaction time. After 5 h the reaction mixture was cooled to room temperature and the volatiles were removed in vacuo. To the dark residue was washed with Et2O (ultrasonication) and again dried in oil pump vacuo. The crude product was used without purification for the next step in the same reaction vessel. Rf (CHCl3/MeOH 4:1)=0.5

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was dried in oil-pump vacuo
  3. customit was ultrasonicated for 1 min
  4. temperaturethe suspension was heated
  5. stirringwith stirring under argon at 125° C. oil bath temperature
  6. temperatureto reflux for 5 h
  7. temperatureheating
  8. customa precipitate is formed after about another 30 min.
  9. customreaction time
  10. customthe volatiles were removed in vacuo
  11. washTo the dark residue was washed with Et2O (ultrasonication)
  12. customagain dried in oil pump vacuo
  13. customThe crude product was used without purification for the next step in the same reaction vessel

Sources & evidence

ORD record
ord-8b70370b462e428392d22d89b195a86b
Source dataset
uspto-grants-2011_11
Patent number
US08063049B2

Reaction notes

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